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Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Akira Yoshimura, Viktor V. Zhdankin

Chemical Reviews · 2024 · Review · CC BY

doi:10.1021/acs.chemrev.4c00303

Abstract

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. Hypervalent iodine reagents are commonly used in synthetically important halogenations, oxidations, aminations, heterocyclizations, and various oxidative functionalizations of organic substrates. Iodonium salts are important arylating reagents, while iodonium ylides and imides are excellent carbene and nitrene precursors. Various derivatives of benziodoxoles, such as azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, and alkenylbenziodoxoles have found wide application as group transfer reagents in the presence of transition metal catalysts, under metal-free conditions, or using photocatalysts under photoirradiation conditions. Development of hypervalent iodine catalytic systems and discovery of highly enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important recent achievement in the field of hypervalent iodine chemistry. Chemical transformations promoted by hypervalent iodine in many cases are unique and cannot be performed by using any other common, non-iodine-based reagent. This review covers literature published mainly in the last 7-8 years, between 2016 and 2024.

Full text

From PubMed Central, U.S. National Library of Medicine, as current on Oct 27, 2026. Paragraph numbers are ours, so an answer can point at one.

Introduction

1Compounds of polyvalent iodine, commonly known as hypervalent iodine reagents, have found wide application in modern organic synthesis as reagents and catalysts. Many features of hypervalent iodine chemistry are similar to the transition metals chemistry, and further exploration of these similarities has led to the creation of new reagents and important synthetic methodologies. In contrast to heavy transition metals, iodine is an environmentally friendly and a relatively inexpensive element (according to the U.S. Geological Survey bulk average price of iodine in the United States from 2017 to 2023 was between $19 and $61 per kilogram, see https://www.statista.com/statistics/1001991/average-price-iodine-us/). Many “metal-free” synthetic applications of hypervalent iodine chemistry are based on the unique oxidizing properties and commercial availability of polyvalent iodine compounds. Compounds of hypervalent iodine are widely utilized in synthetically important oxidations, halogenations, aminations, and many other oxidative transformations of organic substrates. Iodonium salts are important arylating reagents, and iodonium ylides and imides are excellent carbene and nitrene precursors. Particularly important are derivatives of benziodoxoles, such as trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles, and azidobenziodoxoles, which are used as group transfer reagents under metal-free conditions, or under transition metal catalysis, or using photocatalysts under photoirradiation conditions. It is important to emphasize that in many cases the reactions of hypervalent iodine compounds are unique and cannot be performed by using any other common, non-iodine-based reagent.

2The important role of polyvalent iodine in modern chemistry is confirmed by a large number of recently published books and reviews covering several hot areas of hypervalent iodine chemistry. Just in the last 6 years, between 2016 and 2023, three books− and over a hundred major reviews covering different areas of hypervalent iodine chemistry have been published.− Several newly developed synthetic methodologies are based on the similarities between chemistry of hypervalent iodine and the chemistry of transition metals. In particular, hypervalent iodine(III) reagents and catalysts can effectively promote numerous coupling reactions, leading to the formation of new carbon–carbon and carbon–element bonds. The use of hypervalent iodine(III) compounds for the creation of new carbon–carbon bonds was summarized in several reviews.,,, Numerous recent reviews were dedicated to the reactions of hypervalent iodine compounds, resulting in the formation of new carbon–nitrogen bonds.,,,,,−, Construction of C–O, C–S, and C–Se bonds mediated by hypervalent iodine reagents under metal-free conditions was also reviewed. Development of enantioselective catalytic systems based on the unique redox and photoredox properties of iodine(III) has been an important direction in the field of hypervalent iodine chemistry summarized in numerous specialized reviews.,,,,,,,,,−,,

3Application of hypervalent iodine reagents in organic synthesis has been an active area of research. Numerous recent reviews were dedicated to applications of hypervalent iodine in the following reactions: functionalization of alkenes,,, direct C–H bond functionalization,,, chlorinations and fluorinations,,,,,,− phenolic dearomatization reactions,,,,,, rearrangements promoted by hypervalent iodine,,,,, synthesis of spiroheterocycles, applications of hypervalent iodine(III) reagents in organophosphorus chemistry, reactions of hypervalent iodine with boronic compounds, reactions of hypervalent iodine with enol and ynol surrogates, hypervalent iodine compounds in transition metal chemistry,, copper-catalyzed hypervalent iodine-mediated functionalization of unactivated compounds, palladium-catalyzed organic reactions involving hypervalent iodine reagents, organocatalytic group transfer from hypervalent iodine species, glycosylation reactions,, functionalization of carbohydrates, tandem reactions that allow for incorporating the aryl motif into the products through a subsequent one-pot nucleophilic addition or catalytic coupling reaction, and late-stage peptide and protein functionalization. Iodine(III) compounds are commonly utilized for the preparation of various heterocycles via oxidative formation of C–C, C–O, C–N, C–S, N–O, N–N, or N–S bonds.,,,,,,,−,,− Hypervalent iodine reagents are broadly used in total synthesis of natural products.,,,,,

4Numerous reviews have summarized recent synthetic applications of different classes of polyvalent iodine compounds. In particular, aryliodonium salts are important arylating reagents,,,−,− and precursors for Positron Emission Tomography., Iodonium ylides are used as carbene precursors and also as reagents for radiofluorination.,, (Diacetoxyiodo)benzene is an important reagent with various synthetic applications. Numerous recent reviews were dedicated to the application of group-transfer benziodoxole-based reagents.,−,, Trifluoromethylbenziodoxoles are important trifluoromethylating reagents., Azidobenziodoxoles are exceptionally effective reagents for direct azidation of C–H bonds.,, Ethynylbenziodoxoles and vinylbenziodoxoles are useful alkynylating and alkenylating reagents.,,, Weiss’ reagent, [PhI(Pyr)2]2+ 2TfO–, is a synthetically useful oxidizing reagent. Radical and photochemical reactions of benziodoxole derivatives is a hot area of modern hypervalent iodine chemistry.,,, Applications of in situ generated hypervalent iodine reagents in organic synthesis have recently been reviewed.

5Synthetic applications of several new classes of hypervalent iodine compounds have recently been reviewed, such as pseudocyclic hypervalent iodine reagents, benziodoxole sulfonates,, water-soluble hypervalent iodine reagents and their reactions in aqueous medium,,, and recyclable hypervalent iodine reagents.

6New methods for generating derivatives of polyvalent iodine using green chemistry methods were recently reviewed. The anodic oxidation of aryl iodides provides an efficient approach to hypervalent iodine derivatives. Electrochemically generated hypervalent iodine species have been utilized as in-cell or ex-cell mediators for valuable fluorinations and oxidative transformations.,,,− Another environmentally sustainable procedure, the aerobic preparation of hypervalent iodine reagents, is based on the oxidation of iodoarenes by the reactive intermediates generated during autoxidation of aldehydes.

7Iodonium salts have found some industrial application as initiators of polymerization.,, Hypervalent organic polyiodides are used in disinfectants, polarizing films, dye-sensitized solar cells, and precursors to low-density graphitic films. It can be expected that the interest in industrial applications of hypervalent iodine compounds will grow in the future.

8The present review provides an update of our 2016 comprehensive review. The review is limited to synthetic applications of iodine(III) reagents excluding the chemistry of iodine(V). Recent publications in the area of iodine(V) chemistry are mainly represented by numerous papers on routine oxidations of alcohol groups in complex molecules by Dess-Martin periodinate or 2-iodoxybenzoic acid, which is a traditional and well-reviewed area of organic synthesis.,,, Our present review covers literature on organoiodine(III) compounds published mainly in the last 5–7 years, through spring 2024.

Structure and Reactivity of Hypervalent Iodine(III) Compounds

9Because of the large size of the iodine atom, the bonding in compounds of polyvalent iodine is different from the light main-group elements. Computational studies indicate that the typical light p-block elements double bonds formed by the interatomic π-bonding do not exist in the derivatives of polyvalent iodine. Structure and reactivity of polyvalent iodine compounds is usually explained by the presence of a hypervalent bond, a linear, three-center-four-electron bond L—I—L formed by the overlap of the 5p orbital on iodine atom with the orbitals on the ligands L. Hypervalent bond is highly polarized, longer, and weaker compared to a regular covalent bond, resulting in special structural features and reactivity typical of the derivatives of polyvalent iodine. Reactions of hypervalent iodine compounds are commonly discussed in terms of oxidative addition, ligand exchange, reductive elimination, and ligand coupling, which are typical of the transition metal chemistry.− General aspects of structure and reactivity of hypervalent iodine compounds have been discussed in our 2016 review. In summary, the iodine(III) organic derivatives ArIX2 have trigonal bipyramidal geometry with electronegative ligands X in the axial positions, and the aryl substituent and two unshared electronic pairs occupying the equatorial positions. Iodonium salts R2IX with inclusion of a weakly bonded anionic part X of the molecule have a similar distorted trigonal bipyramidal structure. The hypervalent I–X bond length in iodine(III) compounds is longer than an average I–X covalent bond length in compounds of monovalent iodine. Bond angles R–I–R in iodonium salts and iodonium ylides, as well as bond angles R–I–N in iodonium imides, are close to 90°.

10Several structural studies of hypervalent iodine compounds were recently published. Dutton and co-workers have reported numerous studies on structural verification of several common hypervalent iodine reagents.− In particular, the structure of Stang’s reagent, PhI(CN)OTf, was confirmed by X-ray crystallography and determined to be best described as an ion-pair in organic solution. The structure of a complex of PhICl2 with pyridine was established by X-ray, NMR, and theoretical studies. Reinvestigation of the structure of PhI(OTf)2 has demonstrated the actual identity of the reagent being used was PhI(OTf)(OAc). While PhI(OTf)2 is unstable, the para-nitro-substituted derivative, 4-O2NC6H4I(OTf)2, was isolated as a stable compound and characterized by X-ray diffraction. The previously proposed molecule of PhIBr2 was demonstrated to be a mixture of PhI and Br2 on the basis of spectroscopical and computational studies. Waser and co-workers have reviewed X-ray and NMR structural data of ethynylbenziodoxolones (EBXs) reagents and their analogues.

11Reactivity of hypervalent iodine compounds in radical reactions under photochemical conditions was summarized in recent reviews., Numerous recent publications were dedicated to the effects of halogen bonding and Lewis acidity on structure and reactivity of hypervalent iodine compounds.,−

12Theoretical studies of the mechanisms of catalytic and stoichiometric iodine-mediated reactions have been discussed in numerous recent publications.,−

(Difluoroiodo)arenes

13The chemistry and synthetic applications of hypervalent iodine fluorides have been extensively reviewed previously− and summarized in numerous recent reviews.,,,, Two general methods are known for the synthesis of (difluoroiodo)arenes. The first method involves the fluorination of an iodoarene by a fluorinating reagent or a combination of a common oxidant with a fluoride source. The second method is based on the ligand exchange between a hypervalent iodine compound and a fluoride source. These two approaches have been summarized in numerous previous publications.− In the following text, several recently published synthetic procedures for converting iodoarenes to the corresponding (difluoroiodo)arenes are described. Gilmour’s group has published an improved procedure for the synthesis of (difluoroiodo)arenes that was originally reported by Shreeve’s group in 2005., In the improved procedure, para-iodotoluene is mixed with Selectfluor and CsF as an additional fluoride source to give para-(difluoroiodo)toluene in 62% yield. Using Et3N·HF instead of CsF improved the yield up to 92% yield; however, Et3N·HF is a potentially hazardous reagent. Monitoring this reaction by NMR indicated poor conversion after 48 h for iodoarenes with a strong electron-withdrawing groups such as nitro- and trifluoromethyl group, while the conversion was good for iodoarene with electron-donating groups. Murphy’s group reported a large scale procedure for the preparation of para-(difluoroiodo)toluene up to 50 mmol. This procedure involves three steps to prepare para-(difluoroiodo)toluene starting from 4-iodotoluene in 64–72% yield without purification of intermediate products in the first and second steps. Togni’s group developed direct synthesis of (difluoroiodo)arenes from iodoarenes with various electron-withdrawing groups in the ortho-position. It has been noted that the ortho-substituent provides a minor improvement of hydrolytic stability of the obtained (difluoroiodo)arenes and it plays an important role during the reaction with TCICA (trichloroisicyanuric acid) and KF, inhibiting further oxidation of iodine(III) to iodine(V). The reaction of iodoarene 1 and TCICA with KF as the fluoride source affords the corresponding products 2 in good yields (Scheme 1). The authors suggest that the introduction of an electron-withdrawing group at the ortho-position suppresses overoxidation of the produced iodine(III) product to an iodine(V) compound. This methodology provides a mild and efficient approach to electron-deficient (difluoroiodo)arenes and complements the methods of Shreeve’s group and Gilmour’s group which utilize Selectfluor to synthesize electron-rich (difluoroiodo)arenes.

14In 2022, Zhang and co-workers reported a one-step synthesis of (difluoroiodo)arenes using silver difluoride (AgF2) as fluorinating reagent. The reaction of iodoarene 3 with AgF2 is carried out by stirring at room temperature for 1 h to give (difluoroiodo)arenes 4 in good yileds (Scheme 2). In the reaction of 2,4,6-trimethyliodobenzene, slight heating was necessary to give the respective product in 82% yield. A moderately unstable product 4 with methoxy group in the para-position was obtained in 79% yield.

15(Difluoroiodo)arenes can participate in ligand exchange reactions to produce the corresponding products.− Dutton and co-workers used the ligand exchange reaction between p-NO2C6H4IF25 and TMSOTf to synthesize p-NO2C6H4IF(OTf) 6 (Scheme 3), the structure of which was characterized by X-ray crystallography. Previously, the formation of PhIF(OTf) in situ from iodobenzene and xenon fluorotriflate −78 °C was proposed by Stang, Zefirov, and co-workers without any structural proof based on the formation of iodonium salts in the reactions with alkynes. Dutton and co-workers have found that the presence of the nitro group stabilizes compound 6 by preventing degradation via an electrophilic aromatic substitution pathway observed in previous studies of ArI(OTf)2 species. The authors also found that compound 6 reacts with anisole and toluene to give the corresponding diaryiodonium triflates, but it does not react with bromobenzene.

16Bolm and co-workers have reported that p-TolIF2 reacts with NH-sulfoximines, leading to the formation of unstable ligand exchange species as confirmed by 1H NMR, 19F NMR, and ESI-MS. These species were utilized in situ in subsequent reactions with alkenes. The reaction of p-TolIF27 with various NH-sulfoximines 8 and styrenes 9 under Blue-LED with Ru photoredox catalyst gave the corresponding fluoro sulfoximination products 10 in moderate to good yields (Scheme 4). The same authors also reported that when the active species generated by ligand exchange between p-TolIF27 and NH-sulfoximine 8 were stirred in dichloromethane or dibromomethane under Blue-LED without Ru photoredox catalyst conditions, the corresponding chlorinated or brominated products instead of the fluorinated products 10 were formed. A radical mechanism was proposed for these reactions because the products were not formed under dark conditions or in the presence of the radical scavenger such as TEMPO or BHT.

17As a useful fluorination reagent, p-TolIF27 has been used in direct mono- and difluorination reactions of various substrates., As a recent example, Balz-Scheimann fluorination of aromatic diazonium salts with p-TolIF27 in the presence of BF3·Et2O has been reported by Hu and co-workers. Murphy’s group developed a denitrogenative hydrogen-fluorination of benzaldehyde hydrazine derivatives with electron-withdrawing group. The same research group has demonstrated that the reaction of p-TolIF27 with diaryl- or dialkyl phosphine oxides 11 leads to the corresponding phosphate fluorides 12 (Scheme 5), and the reaction with some substrates yields phosphinic acid as a by-product. In the reaction with diethylphosphite, the desired product was obtained in only 34% yield. Although some products 12 are unstable, they can be effectively converted to stable phosphinate esters by treatment with ethanol and isolated. The authors proposed a reaction mechanism involving initial nucleophilic addition of phosphine 13 to the electrophilic iodane 7, forming phosphonium adduct 14. Subsequent nucleophilic attack by fluoride anion on the phosphonium atom in adduct 14 gives intermediate 15, whose deprotonation affords the final phosphoric fluoride 12 (Scheme 6).

18Monofluorination reactions using ArIF2 in situ, in which a fluoride source is added to iodosylbenzene, DIB, or PIFA to form ArIF2 in the reaction system, are also known., Xu and Tang reported that the reaction of alkylsilanes 16 with iodosylbenzene 17 using two fluoride sources, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone hydrofluoride (DMPU·HF) and CsF, gave the corresponding alkyl fluorides 18 (Scheme 7). Using this procedure, a variety of primary alkylsilanes 16 bearing electron-donating or electron-withdrawing substituents in aromatic ring and not-aryl-substituted alkylsilanes 16 were converted to products 18 in good yields. In the reactions of secondary alkylsilanes no products 18 were observed, and the major by-products were alkenes and ketones. The reaction could be carried out on the gram scale. For the mechanism, the results of a radical clock reaction and the addition of TEMPO indicate that radical species are involved. In the presence of CsF and DMPU·HF, PhIF2 is generated from alkylsilane and PhIO with organopentafluorosilicate as the by-product.

19Substrates bearing diazo or benzaldehyde hydrazone moiety react with p-TolIF27, producing products of difluorination.− For example, Murphy and co-workers demonstrated that the reaction of benzaldehyde hydrazone 19 with p-TolIF27 and a catalytic amount of TiF3 yields the corresponding gem-difluorides 20 in moderate yields (Scheme 8). In the reaction without TiF3, the monofluoride is the main product due to insufficient activation of 7. In this reaction, starting compounds 19 react with reagent 7 to form diazo species as the reaction intermediate, which was confirmed by 1H NMR.

20It has been reported that the reaction of aryl-substituted allenes 21 with p-TolIF27 in the presence of a catalytic amount of BF3 yields α-(difluoromethyl)styrenes 22 via 1,2-aryl group shift (Scheme 9). The reactions of para-substituted substrates 21 work best, while the yields of ortho- and meta-substituted derivatives are generally lower. The reaction also proceeds well with allene compounds having an alkyl substituent at the α-position, resulting in the desired products in moderate yields. Futhermore, the reaction was confirmed to proceed under similar conditions for 1-naphthyl and 2-naphthylallenes. To identify which double bond of the allene is involved in this reaction, the authors tested the allene compound with deuterated terminal hydrogens and found that this reaction produced α-difluoromethylstyrene with deuterated hydrogens at the β-position. This result confirmed that no terminal double bond was involved in this reaction. When exocyclic allenes are used as substrates, the ring expansion reaction proceeds and the cyclic products are obtained in moderate yields.

21The synthesis of difluorinated compounds from styrenes via 1,2-phenyl group shift reaction using (difluoroiodo)benzene generated by adding a fluoride source to DIB or PhIO was also reported. For example, Wang and co-workers reported that the reaction of aryl-substituted alkenyl N-methyliminodiacetyl (MIDA) boronates 23 with DIB 24 and HF·Py gave β-difluorinated alkylborons 25 in low to good yields (Scheme 10). When 1,1-disubstituted alkenyl MIDA boronates were used as substrates, α-difluorinated alkylborons were successfully obtained. The authors prepared a deuterated substrate and based on the analysis of products found that 1,2-aryl shift occurs during the reaction. The proposed reaction mechanism starts from the interaction between the double bond of the substrate 23 and (difluoroiodo)benzene generated from PIDA and Py·HF, leading to regioselective vicinal fluoroiodination intermediate 27 via species 26 (Scheme 11). The observed regioselectivity is explained by the ability of the aryl group to stabilize the developing benzylic carbocation. At the next step, departure of the PhI leaving group affords phenonium ion species 28. Finally, the regioselective fluoride attack results in the ring-opening of 28 forming final products 25.

22Difluorination reactions with alkynes using (difluoroiodo)arene generated in the reaction system were reported by Li’s group. They reported that the reaction of aryl alkynylcyclopropanes 29 with pentafluoro(diacetoxyiodo)benzene 30 and an excess amount of HF·Py gave the ring-expanded difluoroalkylidene cyclobutane compounds 31 with (E)-stereoselectivity (Scheme 12). The reaction proceeded efficiently with electron-poor phenyl-substituted alkynylcyclopropanes as substrates but was complicated for the electron-rich aryl-substituted and alkyl-substituted alkynylcyclopropanes, presumably because of the competing oxidation of the substrate under reaction conditions. The proposed mechanism of this reaction involves the initial ligand exchange of compound 30 with HF·Py giving activated iodoarene difluoride 32, which then interacts with the triple bond of substrates 29 to form π-complex 33. At the next step, the regio- and stereoselective fluoride attack on π-complex 33 affords intermediate 34, which undergoes a Wagner–Meerwein-type rearrangement to form cyclobutyl cation 35. Finally, the trapping of this cation by second fluoride leads to stereoselective formation of products 31 (Scheme 13).

23Variuos (difluoroiodo)arenes, ArIF2, can be generated from the corresponding iodoarenes in situ and further reacted with organic substrates using electrochemical or chemical oxidation in the presence of fluoride anions.,

24The McDonald group found that iron(II) complex 36 bearing tris(2-pyridylmethyl)amine react with (difluoroiodo)benzene 37 at room temperature in acetonitrile to form μ-fluorido-diiron(III) complex 38 (Scheme 14). The structure of the obtained compound, which is bridged by fluorine atoms, was determined by X-ray structural analysis. Furthermore, the addition of Lewis acid Sc(OTf)3 to compound 38 resulted in the formation of a monomeric product 39. The same group also found that the reaction of iron(II) complex with tris(2-benzimidazoylmethyl)amine and (difluoroiodo)benzene formed the analogous μ-fluorido-diiron(III) complex.

25Liu and co-workers have reported the palladium-catalyzed oxidative fluorocarbonylation of unactivated alkenes 40 using 2,5-(CH3)2C6H3IF241 (Scheme 15). The reaction is applicable to a variety of alkenes 40, and the addition of MeOH and TMSCHN2 during the reaction yields the corresponding β-fluoro carboxylic esters 42. When H2O or amine were used instead of MeOH and TMSCHN2, β-fluoro carboxylic acids and amides were obtained.

26Additional recent examples of synthetic applications of (difluoroiodo)arenes include the following works: fluorination of cis-1,4-polyisoprene,para-selective benzylation of aryl iodides by the in situ preparation of ArIF2, oxidative fluoroarylation of benzylidenecyclopropanes by in situ generated ArIF2, and hypervalent iodine-mediated gem-difluorination of vinyl halides by in situ generated ArIF2.

(Dichloroiodo)arenes

27From an historical point of view, (dichloroiodo)benzene is one of the first reported hypervalent iodine compounds that has been intensively used as a convenient chlorinating reagent for over a century.− The chemistry and synthetic applications of hypervalent iodine chlorides have recently been reviewed., Numerous synthetic approaches have been developed to (dichloroiodo)arenes, which are the oldest known hypervalent iodine compounds with many practical applications. The classic general approach to (dichloroiodo)arenes is based on reactions of iodoarenes with chlorine gas or chlorine-derived oxidants. Alternatively, (dichloroiodo)arenes can be prepared by ligand exchange reactions of other hypervalent iodine reagents with sources of chloride anion. Ligand exchange reactions of (dichloroiodo)arenes leading to other hypervalent iodine reagents are also known., In recent years, numerous oxidations or oxidative chlorination reactions of various organic or organometallic substrates with (dichloroiodo)arenes have been reported. Computational studies of several chlorination reactions have also been performed.,

28Electrophilic or radical addition or substitution reactions are the most typical reactions of (dichloroiodo)arenes. Chlorinations by substitution reactions have been reported for a variety of aromatic and aliphatic substrates.,− Ibrahim and Adamo reported that the reaction of β-sulfidocarbonyl compounds 43 with a (dichloroiodo)benzene 44 at room temperature for a few minutes afforded the corresponding β-aryl-β-chlorocarbonyl compounds 45 in moderate to good yields (Scheme 16). This reaction is also applied to alkylphenyl sulfides as substrates. When (S)-β-sulfidocarbonyl compounds are used as substrates in this reaction, (R)-β-aryl-β-chlorocarbonyl compounds are obtained with high stereoselectivity. Based on this result, the authors suggest that the reaction mechanism starts from the oxidation of sulfur with (dichloroiodo)benzene, followed by an SN2-like reaction with the chloride anion to afford product 45.

29Dutton and co-workers reported aromatic chlorination reactions of (dichloroiodo)benzene with arenes in the presence of additives.,− They have found that the addition of pyridine as an additive to (dichloroiodo)benzene 44 gives the corresponding tetracoordinated hypervalent iodine compound 46 (Scheme 17), the structure of which was characterized by X-ray structural analysis. The N–I distance is 2.750 Å, which is longer than the covalent distance of a typical N–I bond. Likewise, when tetrabutylammonium chloride is used as an additive instead of pyridine, similar tetracoordinated hypervalent iodine compounds can be obtained. This group has also investigated the mechanism of this reaction using NMR and computational chemistry.

30Reactions using (dichloroiodo)arenes to add chlorine to organic substrates have also been reported. Liu and co-workers reported that the reaction of substituted aromatic isonitrile 47 with (dichloroiodo)benzene 44 in acetonitrile proceeded as gem-dichlorination, yielding the corresponding carbonimide dichlorides 48 in moderate to good yields (Scheme 18). In contrast, the reaction with aliphatic isonitrile did not yield the product of gem-dichlorination. The potential synthetic value of carbonimide dichlorides 48 is that these compounds can be used as synthetic intermediates for 2,2,3,3-tetrachloroaziridine, propyl formimidate, and benzophenone imine. The reaction begins with the hypervalent iodine center of 44 attacking the nucleophilic carbon atom of isonitrile 47 to form intermediate 49. Subsequently, intermolecular nucleophilic substitution results in the formation of a C–Cl bond to produce intermediate 50. Then, intermediate 50 undergoes reductive elimination from the iodine center to give the dichlorination product 48 (Scheme 19).

31Chlorocyclization reactions have also been reported.,, Du and co-workers have reported that the reaction of methyl o-alkynylbenzoate 51 with (dichloroiodo)benzene 44 proceeds with the formation of carbon–oxygen and carbon-chlorine bonds to produce the corresponding 4-chloroisocoumarins 52 (Scheme 20). The reaction proceeds even when ethyl or tert-butyl groups are used instead of methyl groups in the ester moiety of the substrate, and especially when benzyl esters are used; benzyl chloride is obtained as a byproduct, which is an important product in predicting the reaction mechanism. The proposed reaction mechanism of this chlorolactonization reaction starts from the initial coordination of PhICl244 with the alkyne triple bond to give intermediate 53. This is followed by a concerted process involving nucleophilic attack of the carbonyl oxygen atom on the triple bond and the triple bond on the hypervalent iodine center of PhICl244, affording cyclic oxonium ion 54. At the next step, chloride anion nucleophilically attacks the methyl carbon center in 54, leading to intermediate 55. Finally, reductive elimination of iodobenzene in 55 gives the chlorination product 52 (Scheme 21). A similar chlorocyclization reaction using methyl o-styrylbenzoate or methyl o-styrylbenzamide has also been reported. In this chlorolactonization reaction, the corresponding 3,4-dihydroisocoumarins or 3,4-dihydroisocoumarin-1-imines were efficiently obtained.

32It has been reported that (dichloroiodo)benzene reacts with disulfides or diselenides, forming highly reactive sulfenyl chlorides or selenenyl chlorides.− The generated active species can then react with various substrates, leading to the corresponding sulfur or selenium products. For example, Du and co-workers reported that sulfenyl chloride or selenenenyl chloride species, generated in situ by the addition of dichloroiodobenzene 44 to a disulfide or diselenide, react with alkynone (Z)-o-methyl oximes 56, providing the corresponding organoselanyl- or organosulfanyl-isoxazoles 57 (Scheme 22). The authors attempted to isolate the active species, selenyl chloride, and performed NMR measurements. They have also found that the isolated selenyl chloride species can be used to obtain products 57, confirming that it is the key intermediate in this reaction. It has also been reported that when methyl o-alkynylbenzoate was used as a substrate under similar reaction conditions, 4-sulfenyl- or 4-selenyl-substituted isocoumarin products could be effectively obtained. Du and Zhao reported a method for generating organosulfenyl chloride species from sulfoxide and (dichloroiodo)benzene 44 and cyclization reactions using this species.

33Chlorosulfurization reactions as well as intramolecular oxidative cyclization reactions could also be performed using reactive sulfenyl chloride species generated from disulfide compounds and (dichloroiodo)benzene 44. The reaction of a disulfide compound and (dichloroiodo)benzene 44 with p-toluenesulfonyl difluorodiazoethane 58 gives the corresponding products of chlorosulfurization 59 (Scheme 23). The reaction with diselenides instead of disulfides yields the corresponding selenium products. Instead of difluorodiazoethanes 58, diazo compounds with perfluoroalkyl groups, α-diazophosphonates, α-diazoesters, or α-diazoketones can also be used to obtain the corresponding products in good yield.

34Du and co-workers reported that the reaction of KSeCN with (dichloroiodo)benzene 44 and conjugated enamine compounds 60 allows synthesis of 2-amino-1,3-selenazole compounds 61 (Scheme 24). It was suggested that selenocyanogen (SeCN)2 is initially generated from (dichloroiodo)benzene and KSeCN in this reaction. The generated (SeCN)2 reacts with conjugated enamine compounds to give final products 61. Another possible reaction intermediate is chloroselenocyanate, ClSeCN. However, a control reaction of ClSeCN with conjugated enamine 60 gives product 61 only in low yield, confirming that ClSeCN is not a likely intermediate in this reaction.

35The same group has also reported the reaction of chlorothiocyanate ClSCN generated from (dichloroiodo)benzene and NH4SCN., The reaction of o-alkenylbenzoic acids 62 with NH4SCN and (dichloroiodo)benzene 44 gave the corresponding cyanated isobenzofuranones 63 (Scheme 25). The proposed mechanism of this reaction involves consecutive generation of the reactive electrophilic species (SCN)264 and Cl-SCN 65 from PhICl244 and NH4SCN. Next, electrophilic addition of Cl-SCN 65 to the double bond of 62 produces thiiranium ion 66, which is highly reactive toward nucleophilic ring opening. The carbonyl oxygen of the carboxylic acid moiety would attack the more substituted position via the SN1 mechanism to afford intermediate 67. Final deprotonation of this intermediate B gives final product 63 (Scheme 26). When KSeCN was used instead of NH4SCN, the corresponding selenocyanated isobenzofuranones were obtained via chloroselenocyanate, ClSeCN, as active species. Similar to the reactions of KSeCN and NH4SCN, a reaction of tetramethylammonium trifluoromethylselenate, NH4SeCF3, with (dichloroiodo)benzene to generate CF3SeSeCF3 species has also been reported.

36(Dichloro)iodobenzene can also be used in the hydrogen atom abstraction (HAT) reactions. Hu and Yin reported that when 4-methylquinoline 68 and an aliphatic alcohol 69 were reacted with dichloroiodobenzene under LED irradiation, an α-heteroarylation reaction of the aliphatic alcohol occurred and the corresponding secondary alcohols 70 were obtained (Scheme 27). In the presence of radical scavengers such as TEMPO, butylated hydroxytoluene (BHT), or 1,1-diphenylethylene the reaction did not yield products 70, indicating that radicals were involved in this reaction. The authors suggest that the radical species generated in this system participate in selective hydrogen atom abstraction from alcohols.

37(Dichloroiodo)arenes have been used as oxidants of various transition metal complexes. Numerous recent works have reported reactions of (dichloroiodo)arenes with compounds of Fe,, Ni,− Cu, Y, Zr, Ru, Rh,, Pd,− Os, Ir,− Pt,− and Au.− The oxidized organometallic compounds were analyzed by X-ray structural analysis, NMR, UV–vis, luminescence, EPR instrumentation, and DFT computational chemistry to investigate their structure and properties. For example, Gabbai and co-workers reported that the reaction of platinum complex 71 with (dichloroiodo)benzene 44 gave chlorinated complex 72 (Scheme 28). In the presence of dimethylsulfide, complex 72 undergoes a clean photolysis that affords products 71 and 73 (Scheme 29), which is a unique example of a germanium-centered light-induced reduction resulting in the ipso-chlorination of a phenylgermanium species.

38Osakada and Tsuchida et al. have reported that the reaction of gold complexes 74 with (dichloroiodo)benzene 44 yields a mixture of thianthrene 75 and its dimer 76 in moderate yields (Scheme 30). The authors propose that the reaction pathway leading to these two products are derived from two independent mechanisms. One mechanism is the oxidation of the thiantrenyl ligand to form a radical cation intermediate, while the other oxidation reaction is thought to occur at the two Au centers.

[Bis(acyloxy)iodo]arenes

39[Bis(acyloxy)iodo]arenes represent an important class of hypervalent iodine compounds with many practical applications summarized in numerous previous review articles.,,− According to CAS SciFinder, over 2,500 research papers on various synthetic uses of just (diacetoxyiodo)benzene, PhI(OAc)2, were published between 2016 and 2024; however, most of these applications deal with routine oxidative transformations of various organic substrates, which were summarized in earlier reviews. This section mainly covers novel applications of [bis(acyloxy)iodo]arenes in synthetically useful reactions.

40Several general synthetic approaches to [bis(acyloxy)iodo]arenes have been developed. The classical general approach to (diacetoxyiodo)arenes is based on the reaction of an oxidant with an iodoarene in acetic acid solution. Older procedures involve the use of potentially explosive concentrated hydrogen peroxide as the oxidant, while recently developed methods utilize the less explosive oxidants.− Structures of several recently synthesized (diacetoxyiodo)arenes have been characterized by X-ray analysis.,, In addition to structural characterization, a computational study of the oxidizing capacity of various (diacetoxyiodo)arenes has also been reported. Synthesis of several other [bis(acyloxy)iodo]arenes by ligand exchange reactions of (diacetoxyiodo)arenes with different carboxylic acids and study of their solubility in organic solvents has been recently published.

41(Diacetoxyiodo)arenes are efficient oxidants for a variety of organic substrates. A useful feature of these compounds is that they can be easily converted to different hypervalent iodine reagents during the reaction in the presence of appropriate additives. (Diacetoxyiodo)benzene (DIB) 24 is an efficient reagent that can oxidize phenolic compounds to quinone derivatives resulting from subsequent intra-− and intermolecular cyclization or addition reactions.− Such dearomatization reactions can produce quinone products from phenols or anilines.− The cyclization reactions on nitrogen have been reported for dearomatization of aniline compounds in the absence of external nucleophiles. For example, Mal and co-workers reported that the reaction of sulfonamide derivatives 77 with DIB 24 results in the replacement of a tert-butyl group with a new carbon–nitrogen bond to give carbazole products 78 (Scheme 31). This reaction proceeds successfully for substrates with different substituents on the aromatic ring and various sulfonamide groups. The same group has also reported a cyclization reaction on the sulfur atom of thiophenol instead of the nitrogen atom using DIB 24 as the oxidant. Other reactions of anilines using DIB have been reported, such as the synthesis of azo compounds by aniline coupling.,

42Oxidation of aldoximes with DIB 24 generates the corresponding nitrile oxides, which react with alkenes or alkynes to give the corresponding heterocyclic compounds.− The in situ generated nitrile oxides can also be trapped by the reaction with acetic acid, leading to the formation of N-acetylamides. For example, the reaction of α-MIDA borylaldoximes 79 with DIB 24 in the presence of acetic acid yields the corresponding N-acetoxyamides 80 in good yields (Scheme 32). The resulting N-acetoxyamides 80 can be further converted to boron-containing hydroxylamines by appropriate treatment. Oxidation of ketoximes with DIB 24 has also been reported.,

43Various reactions of amines with DIB 24 resulting in the oxidation of nitrogen atom have been reported.− For example, Murai and co-workers reported an oxidative rearrangement reaction of amines promoted by DIB. In this reaction, secondary amines 81 react with DIB in trifluoroethanol solution and are subsequently treated with a reducing agent to obtain rearrangement products 82 in moderate to high yields (Scheme 33). The proposed reaction mechanism includes the in situ generation of N–I(III) intermediate 83 which further undergoes 1,2-carbon-to-nitrogen migration, leading to iminium species 84. These species are reduced by NaCNBH3 to afford final products 82 (Scheme 34). The same group has also reported the oxidative rearrangement reactions using primary amines.

44Preparation of nitrile compounds by oxidative cleavage of amines by DIB has been reported. The reaction of 5-aminopyrazoles 85 with DIB 24 gives the corresponding 1,2-diaza-1,3-dienes 86 (Scheme 35)., The authors believe that radical intermediates are not involved in this reaction because in the presence of radical scavengers such as TEMPO and BHT the reaction affords products 86 in unchanged yields. Bao and Sun reported a similar oxidative cleavage of the amine moiety of 2-aminobenzothiazole upon treatment with DIB, leading to a conjugated nitrile intermediate which could be trapped by a [4 + 2] cycloaddition reaction with alkenes. The reaction of 2-aminobenzothiazoles 87 with DIB 24 in the presence of alkenes 88 yields dihydro-1,4-benzothiazines 89 (Scheme 36). The key intermediate in this reaction appears to be the conjugated cyano compound 90 formed by the oxidative cleavage of 2-aminobenzothiazole with DIB.

45Luo and He have reported that a denitrogenation reaction occurs when a hydrazone is treated with DIB. The reaction of N-arylsulfonylhydrazones 91 with DIB 24 under basic conditions yields denitrogenated vinylsulfone products 92 (Scheme 37). Since this reaction does not yield products 92 in the presence of TEMPO, the authors suggest that the reaction mechanism involves radicals.

46Several Hofmann rearrangement reactions of cyclic imides, or amides− with hypervalent iodine reagents were previously reported. More recently, the Patureau group reported that the reaction of benzotriazole in the presence of DIB with N-methoxyamide as a substrate leads to a nitrogen–nitrogen coupling reaction. In this reaction, DIB 24 and N-methoxy amide 93 are added to the benzotriazole 94 to obtain the nitrogen–nitrogen cross-coupling compound 95 (Scheme 38). Aromatic and aliphatic N-methoxyamides 93 can be used in this reaction. In this reaction, if N-methoxyamide and DIB were reacted for 16 h and then benzotriazole was added, products 95 were not formed. In contrast, when benzotriazole and DIB were reacted for 16 h and then N-methoxyamide 93 was added, the desired product 95 was obtained. The authors suggested that the amide substrates decompose in the presence of DIB, while benzotriazole is stable under these conditions.

47Reactions of alkoxy amides with long alkyl chains with alkynes or alkenes instead of methoxy groups have also been reported., When DIB 24 is reacted with alkoxyamides 96 with an alkyne moiety, an intramolecular cyclization reaction proceeds in 1 min to give the corresponding cycloheptatriene-fused lactams 97 (Scheme 39). A similar cyclization occurs when alkenes are used instead of alkynes. The authors have used DFT calculations to explain the reaction mechanism.

48DIB has been used as an effective reagent in the oxidation reactions of urea derivatives. Jeffrey and co-workers reported that a [2 + 3] cycloaddition reaction proceeds when DIB 24 is added to a mixture of N,N-dibenzyloxyurea 98 and an indole 99, yielding the corresponding imidazoloindole products 100 (Scheme 40). The reaction mechanism includes initial formation of a diazaoxyallylic cationic species 101 by the oxidation of N,N-dibenzyloxyurea 98 with DIB 24, which then reacts with indole 99 to produce a zwitterionic intermediate 102, followed by an intramolecular cyclization reaction to form final product 100 (Scheme 41). Romo and co-workers have reported a similar [2 + 3] cycloaddition reaction with indole of a compound with a guanidine skeleton instead of urea.

49It is known that DIB is an effective oxidant not only for nitrogen compounds but also for sulfur compounds.− The oxidation of organic sulfides to sulfoxides using DIB has been well-documented. On the other hand, the reactions in which sulfur compounds react with nitrogen compounds in the presence of DIB to form various products with a sulfur–nitrogen bond have also been reported recently.− For example, Willis and co-workers reported that the reaction of sulfinamidines 103 with DIB 24 and amines 104 yielded sulfonimidamide products 105 with new S–N bonds (Scheme 42). The reaction proceeds efficiently with sulfinamidines bearing various functional groups and with a variety of amines. This chemistry is suitable for the preparation of several known sulfondiimidamide-derived medicinal agents. The same group has also reported a similar reaction utilizing sulfinamides instead of sulfinamidines. resulting in the corresponding sulfonimidamide products.

50Recently, Lu’s group reported the synthesis of sulfinimidate esters from sulfenamides. In this reaction, the addition of sulfonamide 106 and alcohol 107 to DIB 24 efficiently produced sulfinimidate ester 108 (Scheme 43). A variety of alcohols can be used in this reaction; even when the alcohols derived from natural products (e.g., the hair growth stimulator RU58841 and the estrogen receptor modulator (SERM) ospemifene) are used, the corresponding products 108 are obtained in moderate yields.

51It was reported recently that the reaction of allyl compounds with DIB, amine, and a catalytic amount of a selenium reagent leads to a metal-free C–H amination of the allylic position.− For example, a vinylsilane 109, a sulfonamide 110, and a catalytic amount of selenium reagent 111 react with DIB to form compound 112 with the aminated allylic position (Scheme 44). This reaction also proceeds efficiently when a pinacol boronic acid derivative is used instead of the vinylsilane. The proposed mechanism of this reaction involves initial generation of a reactive selenium bis(imide) species 113, which undergoes a sequential ene reaction to yield intermediate 114, followed by a [2,3]-sigmatropic rearrangement affording aminated product 115. Final product 112 is formed from intermediate 115, while the selenium catalyst is regenerated from DIB 24 and amine 110 to form selenium bis(imide) species 113 (Scheme 45). The same group has also recently reported that selective C–H amination reactions can also occur for allyl compounds without silyl or boron group substituents.

52DIB and its derivatives are useful reagents for intramolecular cyclization reactions, and numerous cyclization reactions leading to various ring structures have been reported in recent years.,− Cuny and co-workers reported an oxidative cyclization of protected acrylamides 116 using DIB 24 in acetic acid to give oxazolidine-2,4-dione derivatives 117 in good yields (Scheme 46). The suggested reaction mechansim includes initial coordination of DIB 24 with the double bond of acrylamides 116 via intermediate 118 (Scheme 47) followed by cyclization via elimination of isobutylene to form intermediate 119. Finally, nucleophilic substitution of the hypervalent iodine leaving group in 119 with an acetate anion affords final product 117.

53Activation of DIB by the addition of Brønsted acid or Lewis acid has been well-documented; however, the structure of the activated species was not reliably confirmed. In 2016, Shafir and co-workers were the first to report the X-ray structure of PhI(OAc)OTf produced by the ligand exchange reaction between DIB and TMSOTf. This reagent was further converted by dimerization to the Zefirov’s reagent [PhIOIPh](OTf)2, the structure of which was also revealed for the first time by X-ray analysis. Furthermore, when BF3 was added to DIB instead of TMSOTf, the structure of the activated PhI(OAc)2-BF3 complex was also confirmed by X-ray analysis, and the reactivity of this complex was experimentally investigated along with NMR studies and DFT calculations. In recent years, a number of sigmatropic rearrangement reactions of unsaturated compounds promoted by DIB-BF3 or DIB-TMSOTf have been reported.− Several examples of such reactions of DIB with various unsaturated compounds are shown in Scheme 48. In these reactions, DIB 24 reacts with substrates 120, 123, 126, 129, and 132 to form the corresponding intermediates 121, 124, 127, 130, and 133, which then undergo intramolecular sigmatropic reactions to yield final products 122, 125, 128, 131, and 134. These reactions can also be carried out using ArI(OAc)2 with various substituents in the Ar ring. On the other hand, it has been reported that, under similar reaction conditions, when benzylsilane or benzylborate compounds are used instead of allylsilanes 123, the insertion reaction proceeds to the para-position instead of the ortho-position.,

54Wengryniuk and co-workers reported the sigmatropic reaction using PIFA and its derivatives instead of DIB. In this reaction, the addition of pyridine and TMSOTf to 2-cyclohexen-1-one 135 followed by the addition of PIFA 136 leads to the rearrangement product 137 (Scheme 49). The reaction proceeds efficiently even when PIFA with various functional groups is used in this reaction. The proposed mechanism of this reaction involves the formation of β-pyridinium silyl enol ether 138 from pyridine and TMSOTf followed by ligand exchange reaction with PIFA 136 to form an intermediate 139, which is then converted to final product 137 via a [3,3]-sigmatropic reaction (Scheme 50).

55Yorimitsu and co-workers reported a sigmatropic reaction using naphthol derivatives. In this reaction, 2-(diacetoxyiodo)naphthalene 140 reacts with 2-naphthols 141 in acetic acid to afford the corresponding binaphthyl derivatives 142 in moderate yield (Scheme 51). The proposed mechanism of this reaction includes the initial ligand exchange of reagent 140 and 2-naphthol 141 to form intermediate 143, sigmatropic reaction of which yields product 142. The authors have also found that products 142 can be converted to π-extended furan compounds upon heating under basic conditions.

56Szpilman’s group reported the umpolung Morita-Baylis-Hillman (MBH) reaction of α,β-unsaturated compounds using DIB. The reaction of compounds 144 with DIB 24 using pyridinium p-toluenesulfonate (PPTS) as a nucleophile, followed by treatment with triethylamine, yields the α-tosylated products 145 in moderate yield (Scheme 52). On the other hand, when acetic acid is used as a nucleophile, an acetoxylation occurs at the α-position, and the initial acetoxylated product is then converted to a 1,2-diketone by passing through a basic column. The proposed mechanism of this reaction includes the initial addition of pyridine and DIB 24 to unsaturated compound 144, producing an electrophilic enolonium intermediate 146, followed by the reaction with tosylate anion to form adduct 147, which is further converted to final product 145 by triethylamine (Scheme 53). The intermediate adduct 146 was detected by NMR. Maulide and co-workers reported the use of DIB and silyl enol ether as the starting material to generate enolonium intermediates, followed by the introduction of an Ar group at the α-position via 1,2-rearrangement of the Ar group.

57Various reactions resulting in a regioselective introduction of a substituent at the C5 position of 8-aminoquinolinamides 148 using DIB or other (diacyloxyiodo)iodobenzene reagents have been reported.− Typical examples of such reactions leading to the corresponding products of insertion 149–152 in moderate yields are shown below (Scheme 54). It was suggested that the mechanism of these reactions involves initial SET interaction of an iodine(III) reagent with 8-aminoquinolinamides 148. Similar insertion reactions using metal reagents have also been reported., Other heterocyclic substrates such as imidazopyridines− and quinoxalinones, have been used for the analogous regioselective insertion reactions at the C3 position.

58A common methodology involves combining DIB with various additives to generate new active species, which then react with the substrate.− In particular, it has been reported that the addition of halide anion sources to PhI(OAc)2 results in the formation of hypervalent iodine halide species PhI(OAc)X or PhIX2 which are further used for halogenation of various substrates in situ. These species can be used for halogenations of substrates with sp2 carbon,,,,,,,sp carbon,,, and sp3 carbon atoms. It has been reported that halogenation-cyclization reactions of alkenes can be used for the synthesis of various cyclic products.,,,, For example, Bolm and co-workers have developed a method for halocyclizations of S-alkenylsulfoximines. Treatment of unsaturated NH-sulfoximines 153 with a combination of DIB 24 and potassium iodide leads to the formation of S-oxides of dihydro isothiazoles 154 (n = 1) or tetrahydro-1,2-thiazines 154 (n = 1) in good yields with high diastereoselectivities and regioselectivities (Scheme 55).

59This methodology has also been used for halogenation at the nitrogen atom. The generated nitrogen-halogen bond is relatively unstable and quickly breaks by a radical pathway, resulting in inter-, or intramolecular amination reactions.− Some representative examples of intramolecular amination reactions are shown below (Scheme 56). These amination reactions can proceed at the sp2 or the sp3 carbon atom. It has also been reported that this reaction can be carried out efficiently under photochemical conditions such as visible light and LEDs. DIB and halogen additives can react with various amides, e.g., 155, 157, 159, 161, and 163, to obtain the corresponding cyclization products 156, 158, 160, 162, and 164 in low to high yields. Proposed mechanism of these reactions generally includes homolytic cleavage of the initially formed halogen-nitrogen bond to form a nitrogen radical, which then undergoes an intramolecular HAT followed by the cyclization reaction.

60The Nagib group reported various amination reactions utilizing imidate derivatives prepared from nitriles and alcohols.− In these reactions, DIB and NaI are added to imidates to form oxazoline products in the mixture, which are then treated with HCl to obtain the desired β C–H amination products (Scheme 57). The authors found that imidates derived from various alcohols can be used as substrates in this reaction. The same group has also reported that a similar reaction proceeds using a catalytic amount of I2 instead of a stoichiometric amount of NaI. They have also found that the reactions using stoichiometric amounts of CsI yield oxazole products in moderate to high yields. In these reactions, an N–I intermediate 168 is formed from imidate 167, DIB 24, and an iodine additive, followed by homolytic cleavage of the N–I bond to give nitrogen radical species 169 which then undergoes an intramolecular 1,5-HAT reaction, leading to the carbon radical species 170 and the final amination products (Scheme 58). In addition, the authors have also performed a Hammett plot study using 2-arylethanol imidates for the HAT reaction, and the negative slope of the Hammett equation indicated that the reaction proceeded faster for the electron-donating group than for the electron-withdrawing group. This result suggests that the electron-donating group at the para-position stabilizes this transition state, while the electron-withdrawing group has the opposite effect.

61In 1998–2005, Kirschning and co-workers reported the preparation and synthetic application of several polymer-supported halogenate(I) complexes by the DIB-promoted oxidation of polystyrene-bound halides., Recently, these reagents were used for the generation of polymer-supported azides which were utilized as reagents in photochemical azidation reactions.−

62A reaction utilizing a carboxylic acid as the additive has also been reported. In this reaction, the ligand exchange between DIB and carboxylic acid produces iodine(III) species with a new acyloxy group ligand, which reacts with the substrate as a reagent to perform the desired reaction.− The objective of this exchange reaction is not to introduce a new acyloxy group to the substrate, but to add a specific alkyl radical to the reaction substrate, which is generated by decarboxylation of the corresponding acyloxy group under reaction conditions. For example, when DIB 24, alkenes 171, and difluoroacetic acid 172 reacted under blue LED irradiation, hydrodifluoromethylated products 173 were obtained (Scheme 59). In this reaction, the iodine(III) reagent produced from DIB and difluoroacetic acid is decarboxylated during the reaction under blue LED irradiation to form difluoromethyl radicals, which further react with alkenes to give the desired product. The reaction solvent, THF, is used as a hydrogen atom source for the target product (Scheme 59). An example of a similar reaction producing alkyl radicals using sodium alkylsulfinate as an additive has been reported.−

63The other examples of reagent combinations DIB/additive leading to various reactive species in the reaction mixture include the following: DIB/NaN3,, DIB/K(Na)SCN,− and DIB/CF3(HCF2)SO2Na.,

64Phenyliodine bis(trifluoroacetate) (PIFA) is a reagent with a generally similar DIB reactivity. Like DIB, this reagent is used as an efficient oxidant for various organic substrates. For example, the oxidation of phenols using PIFA has been reported in numerous publications.,,− Treatment of a phenolic compound 174 with PIFA 136 affords bicyclo[3.2.1]octane derivative 175 in 72% yield (Scheme 60). This reaction involves an intramolecular [5 + 2] cyclization of the initial product of dearomatization of phenol 174 with PIFA 136, leading to final product 175. The introduction of substituents with electronic and steric effects at the 4- and 5-positions of the substrate yielded the desired products in moderate yields. It has also been reported that the yield of product 175 is slightly lower when DIB is used instead of PIFA in this reaction.

65The use of PIFA for cyclization reactions of various substrates has been reported.− Shibata’s group reported that the reaction of amino compounds 176 with PIFA and a catalytic amount of I2 under photoirradiation affords cyclization products 177 in moderate to high yields (Scheme 61). It was demonstrated that PIFA under photoirradiation conditions was the only effective reagent in this cyclization. When DIB was used instead of PIFA, only trace amounts of product 177 were obtained, and that the desired product was not obtained at all without light. The authors suggest that the generated from PIFA and I2 trifluoroacetyl hypoiodite IOCOCF3 represents the active species in this reaction.

66PIFA can be used as an intermolecular coupling reagent.− The dimerization of substrates by oxidative dearomatization with PIFA was reported by Hajra and co-workers. The reaction of 2H-indazole 178 as a substrate with PIFA afforded N-1-indazolyl indazolones 179 in moderate to high yields (Scheme 62). The authors suggest that the trifluoromethyl acetate ligand of PIFA serves as the oxygen source in product 179. They also believe that this reaction proceeds by SET mechanism.

67In addition to these reactions, numerous oxidations with PIFA have been reported in the previously published review articles.,

68DIB, PIFA, and other [bis(acyloxy)iodo]arenes are commonly used as oxidizing reagents in the presence of various transition metal caatalysts.,,, In the past few years, numerous oxidations catalyzed by compounds of transition metals such as palladium,− copper,,− silver,, gold,− nickel,− cobalt,, manganese,− rhodium,, platinum,, vanadium, rhenium, ruthenium, and iron− have been reported. Beccalli and co-workers reported palladium-catalyzed enantioselective and regioselective oxidative cycloaddition reactions of alkenol compounds. In this reaction, the addition of iodine(III) reagent and palladium catalyst to alkenol 180 in the presence of a catalytic amount of pyridinyl oxazoline ligand 181 gives the corresponding six-membered ring product 182 enantioselectively (Scheme 63). The addition of the ligand is important in this reaction. In the absence of ligand, product 182 is obtained in a low yield in a complex mixture of by-products.

69The palladium(II)-catalyzed reactions of DIB or PIFA with the same substrate but leading to different products were reported by Broggini and Poli. For example, the reaction of N-tosylglycine N′-crotyl-N′-benzylamide 183 with DIB and catalytic amounts of Pd(OAc)2 gave 5-vinylpiperazinone 184 in 50% yield (Scheme 64). The same substrate reacts with PIFA under the same conditions to afford 2-vinylimidazolidinone 185 in 78% yield. The authors have used this difference in reactivity with DIB and PIFA to synthesize several new products.

70Gao and Song reported that the reaction of bicyclic epoxides with DIB in the presence of a copper catalyst leads to rearranged products. The reaction of 1,3-azasilinyl-4-epoxides 186 with DIB and CuI yielded ring-restructured aldehydes 187 (Scheme 65). Additional experiments have demonstrated that this reaction is specific for silicon compounds. According to 13C NMR and ESI-MS measurements, this reaction in the presence of 18O-water yielded products with Si–18O bond, which confirms that the oxygen atom in the aldehyde product was oxygen from epoxide. Based on the control experiments, the authors suggest that the in situ generated Cu(II) intermediates are possible active species in this catalytic reaction.

71Copper-catalyzed C–H amination reactions were reported by Cai and Xia. In the reaction of 2H-indazole 188 and indazol-3(2H)-one 189 with DIB 24 and a catalytic amount of copper(II) triflate, product 190 aminated at the C3 position of 2H-indazole was obtained (Scheme 66). In the presence of a radical scavenger such as BHT, an adduct of indazol-3(2H)-one 189 and BHT was isolated, implying that radicals derived from indazol-3(2H)-one were involved in the reaction. The role of DIB in this reaction is in the reoxidation of Cu(I) to Cu(II) active species.

72Nevado’s group reported a successful synthesis of an Au(III) complex from Au(I) compound using the oxidizing power of DIB. The reaction of DIB with polyfluoroaryl gold(I) compounds 191 gave trans-diacetoaryl gold(III) complexes 192 in moderate to high yields (Scheme 67). Reaction of these gold(III) complexes 192 with excess amounts of TMSCN led to ligand exchange reactions, yielding a mixture of trans- and cis-type gold(III) complexes 193 with cyano ligand. The authors have also performed a reductive elimination reaction of the trans-gold(III) complex by heating in 1,4-dioxane solution to afford the corresponding polyfluorinated benzonitriles in high yield.

73Photocatalytic reactions of DIB have also been reported.,− The proposed mechanism of these reactions involves the initial interaction of a photocatalyst with light to generate excited chemical species. The excited species are then oxidized by an iodine(III) reagent to form active species. The active species reacts with the substrate and returns to the original catalytic species to initiate the next cycle. For example, it has been reported that DIB 24 and quinoxaline-2(1H)-one 194 react under 24 W LED irradiation in the presence of a photocatalyst to yield product 195 with a methyl group introduced at the C3 position of quinoxaline-2(1H)-one (Scheme 68). DIB serves as the source of the methyl group in this reaction, and when a different carboxylic acid is added, a product with an alkyl group of the carboxylic acid introduced instead of a methyl group is obtained. Products 195 were not obtained in the presence of TEMPO, which indicated that radical species were involved in the reaction mechanism.

Iodosylarenes

74Iodosylbenzene and other iodosylarenes have been widely used as effective oxidizing reagents for over a century.− Iodosylarenes in general have a polymeric structure and are insoluble in common organic solvents., In the presence of a polar protic solvent such as an alcohol, iodosylbenzene dissolves, forming new hypervalent iodine species with an alkoxy group as a ligand. The structure of some of these alkoxy-substituted species was confirmed by X-ray analysis; however, these compounds are unstable and quickly revert back to iodosylbenzene. Mckenzie and co-workers reported the crystal structure of iodosylbenzene using a combination of various analytical instruments and crystallographic approaches. Based on the structural analysis, the authors consider that not only the intermolecular interactions of O–I···O–I but also the C–H···π interactions between adjacent phenyl groups contribute to the insolubility of PhIO. Some iodosylbenzene derivatives can dissolve in common organic solvents due to the presence of additional intramolecular interactions. The soluble iodosyl compounds have a basic oxygen atom and can form complexes with acidic alcohol such as HFIP; the structure of such a complex was characterized by NMR and X-ray crystallography. Iodosyl compounds with pseudocyclic structure that form the complex with TFA have also been reported. Recently, it has been reported that iodosyl compounds form complexes with various metals, and their structures have been further investigated by X-ray crystallography.,− A common synthesis of iodosylbenzene involves the treatment of (diacetoxyiodo)arenes with a base. In a recently reported method, iodosylarenes are conveniently prepared by the reaction of iodoarenes with sodium hypochlorite under CO2 conditions.

75Iodosylarenes, similar to (diacetoxyiodo)arenes, can be used as efficient oxidizing reagents. Oxidations of phenols,, anilines,− alcohols and enolates− have been recently reported. For example, Gu and co-workers reported that the reaction of 9H-fluorene-9-ols 196 with iodosylbenzene 17 gave the corresponding oxo-spiro compounds 197 (Scheme 69). The resulting compounds could be converted to biphenyl products by acid treatment. The authors suggested that a phenolic compound 198 is initially formed from the starting material 196 and PhIO 17, which is further converted to final product 197 by oxidative dearomatization.

76Stockman and co-workers reported synthesis of sulfonimidates from sulfinamides using PhIO as an oxidant. Sulfinamides 198 react with PhIO in an alcohol solution to form alkoxy-substituted sulfonimidates 199 in moderate to high yields (Scheme 70). Weakly nucleophilic alcohols and unsaturated alcohols can be used in this reaction. The resulting products 199 can be converted to sulfoximines by reaction with Grignard reagents.

77Iodosylarenes are commonly utilized as an oxidant in the construction of heterocyclic molecules. It is especially useful for intramolecular cyclizations of various unsaturated precursors.− It has been reported that the reaction of N-cyclohexenylamide 200 with iodosylarene and BF3 yields monofluorinated five-membered fused oxazolines 201 and 202 (Scheme 71). In this reaction, BF3 not only activates the ArIO but also serves as a fluorine source. The position of fluorine introduction depends on the substituents in the substrate. When substituent R2 = H at the 4-position of the cyclohexenyl moiety in substrate 200, fluorine is introduced into the ring of product 201, and when substituent R2 ≠ H, fluorine is introduced outside the ring of the product 202. In such regioselective fluorination reactions, the stability of the intermediate carbocation is believed to be important. When acetonitrile was used as the reaction solvent, the Ritter-type reaction proceeded and the acetamide group was inserted instead of fluorine, indicating that carbocation was formed during reaction.

78Iodosyl compounds are useful reagents not only for intramolecular reactions but also for intermolecular reactions. For example, the reaction of 1,3-dicarbonyl compounds in the presence of carboxylic acids leads to α-acyloxylated products. Recently, Dong and co-workers reported that the reaction of a 1,3-dicarbonyl compound, β-oxoamide, with a cyclic amidine gave a polysubstituted imidazolidin-2-one. Chmielewski and Li have reported the insertion reaction of amines into conjugated macrocycles using PhIO. When the nickel-centered macrocycle 203 was treated with amine 204 and an excess amount of PhIO 17, 10-azacorroles 205 were obtained (Scheme 72). Structures of several products 205 were established by X-ray analysis.

79Iodosyl compound can be converted to new hypervalent iodine active species in the presence of appropriate additives. For example, in alcohol solutions, alkoxy-substituted hypervalent iodine species are generated., Du and Zhao reported a lactonization reaction promoted by these iodine(III) species. When 2-(1-phenylvinyl)benzoic acid 206 is reacted with PhIO in alcohol as a solvent under heating, the corresponding lactones 207 are obtained (Scheme 73). In this reaction, the generated dialkoxyiodine(III) species react with the alkene moiety of the starting material, followed by 1,2-migration of the aryl group and alkoxylation, leading to final products. The reactions utilizing iodine(III) species generated in the presence of such additives as diselenide,, iodine source,, AlX3 (X = NO3, Cl, Br),− carboxylic acid, and fluoride source,,− have been reported.

80Reactions of PhIO in the presence of metal compounds such as Mn,− Cu, Fe, Ru, and Co as catalysts have been reported. For example, Feng and Liu reported the asymmetric epoxidation of alkenes using Co catalysts with chiral ligand. When cyclic trisubstituted alkenes 208 react with PhIO 17 and Co catalysts in the presence of chiral ligand 209, the corresponding epoxy products 210 are obtained with high enantioselectivity (Scheme 74). The reaction also proceeds with acyclic alkenes. The authors have detected the generation of intermediate Co–O species from PhIO and Co catalyst during this reaction by ESI mass spectrometry and have investigated the enantioselectivity by DFT calculations.

[(Diamido)iodo]arenes

81[(Diamido)iodo]arenes are efficient reagents for introducing amido group into various organic substrates. These compounds are generally prepared by a ligand exchange reaction between (diacetoxyiodo)arenes and a trimethylsilyl-substituted amide or imide. Several (diamidoiodo)arenes have been investigated by X-ray structural analysis. Compounds with bis(trifluoromethanesulfonyl)imide group as a ligand were also synthesized, but their structures were not reliably confirmed in earlier works. Recently, Dutton and co-workers have reported X-ray structure of para-nitro-substituted (diamidoiodo)arene 212, which was prepared by the reaction (difluoroiodo)arene 211 with TMSNTf2 in CDCl3 (Scheme 75)., The X-ray structure revealed that the I–N bond distance of this compound is longer than other previously reported I–N bonds. The authors have shown that compound 212 has better oxidizing power than 4-NO2C6H4I(OTf)2. For example, 3-methylcyclohexene is oxidized to toluene by 4-NO2C6H4I(NTf2)2 but not by 4-NO2C6H4I(OTf)2. The high oxidation potential of 4-NO2C6H4I(NTf2)2 is also confirmed by calculations using the B3LYP/6-311+G(d,p) method.

82Muñiz and co-workers reported that the reaction of indole compounds 213 with PhI(NTs2)2 gave products 214 aminated at the 2-position of the indole (Scheme 76). When PhI(NMs2)2 or PhI(NTsMs)2 is used instead of PhI(NTs2)2, the corresponding products 214 are also obtained in good yields.

83A saccharin analogue of PhI[N(SO2R)2]2 has been prepared and investigated. It has been demonstrated that this reagent can react with indole derivatives 215 in the presence of a catalytic amount of I2 under light irradiation to produce compound 216 with saccharin moiety introduced at the 2-position of the indole (Scheme 77). This iodine(III) reagent serves as an oxidant and a nitrogen source in this reaction. Under similar reaction conditions, it can be used for regioselective introduction of saccharin moiety into various other heterocyclic compounds.

[Acyloxy(amido)iodo]arenes

84[Acyloxy(amido)iodo]arenes can be generally synthesized by adding an equal amount of a trimethylsilyl-substituted amide or imide to (diacetoxyiodo)arene. The structure of these compounds was confirmed by X-ray crystallography., [Acyloxy(amido)iodo]arene can be further converted to [(diamido)iodo]arene by adding a second equivalent of trimethylsilyl-substituted amide. [Acyloxy(amido)iodo]arenes are useful as the amidation reagents similar to [(diamido)iodo]arenes. For example, it has been reported that the reaction of alkoxyalkynes 217 with PhI(OAc)NTs2 under heating efficiently affords NTs2-substituted 2,5-dihydrofuran 218 (Scheme 78). The proposed reaction mechanism involves the reaction of PhI(OAc)NTs2 with alkyne 217 to form intermediate alkynyliodine(III) species 219. Subsequent Michael addition of the NTs2 anion generates alkylidene carbene 220, which is further converted to final product 218 by intramolecular 1,5-C–H insertion (Scheme 79).

85PhI(OAc)N(SO2R)2 reagents can be be generated and utilized in situ. For example, the reaction of aromatic alkynes 221 with DIB 24 and dibenzenesulfonimides provides the corresponding ynamides 222 in moderate yields (Scheme 80). In this reaction, alkylidene carbene is also generated as a key intermediate, but because aryl-substituted alkynes are used, the common 1,2-rearrangement occurs, leading to alkynes 222.

86An example of the formation and use of the PhI(OAc)NTs2 reagent in situ has been reported for the cyclization of N-allylamides. The reaction of DIB 24 and bis-tosylimide with N-allylamides 223 gives the corresponding oxazolines 224 (Scheme 81). Under similar conditions, the reaction of N-allylthioamides afforded thiazolines. In these reactions, the generated PhI(OAc)NTs2 species activate the alkene moiety, initializing the cyclization.

Iodonium Imides

87Iodonium sulfonimides, PhI = NSO2R, can be generally synthesized from DIB and sulfonamides under basic conditions and are known to be insoluble in common organic solvents due to the polymeric structure. It has been demonstrated that the introduction of a coordinating substituent in the ortho-position of the phenyl ring improves the solubility and stability of iodonium imides and improves their reactivity. The most common synthetic application of these reagents is the transfer of the imino group to the substrate, but it is also known that they can be used as oxidants. Typical imino group transfer reactions are represented by the oxidative iminination of various transition metal compounds, such as complexes of Cu, Fe,− and Ag. For example, Campbell and co-workers reported that the addition of PhINTs to a Ag(I) complex 225 gave an Ag(II) complex 226 (Scheme 82), whose structure was determined by X-ray crystallography. In a similar reaction of Ag(I) complex 225 with an excess amount of PhINSO2Ph, the corresponding Ag(II) complexes containing N(SO2Ph)2 were obtained in high yields and confirmed by X-ray analysis. Furthermore, the authors have confirmed by NMR that a Ag(III) complex can be generated in the system from an excess amount of iminiodane with Ag(I) complex, and they suggested that this is the active species in the silver-catalyzed aziridination of alkenes by PhINTs.

88Typical metal-catalyzed reactions of iminoiodanes include aziridination of alkenes, C–H amination, and transamination toward heteroatoms. In recent years, aziridination reactions utilizing various metal catalysts have been reported.− There have also been numerous reports on the methodologies based on generating iodonium imide species in situ to perform these reactions.− In addition to aziridination of olefins, aminocyclopropanation reactions of allenes are also known. Pérez and co-workers reported that the reaction of allenes 227, alcohols, and iminiodanes in the presence of silver catalysts gave the corresponding aminocyclopropanated compounds 228 in moderate yields (Scheme 83). The structures of the products have been determined by X-ray crystallography. The authors have also reported that, under similar conditions, the reaction without the alcohol yields azetidine when the substrate is an aromatic allene, while the reaction with an aliphatic allene yields methylene aziridine.

89Several examples of C–H amination reactions using iodonium imides with various metal catalysts have been investigated, and stereoselective and regioselective aminations have been reported.− For example, White and co-workers reported a benzyl position selective C–H amination reaction utilizing Mn catalyst. The reaction of aromatic compounds 229 proceeds in the presence of Mn catalyst and iodine(III) reagent to give the corresponding C–H amination products 230 (Scheme 84). This reaction can also be used for C–H amination of compounds with various natural product skeletones. A characteristic feature of the selectivity of this amination is that when the substrate has an electron-rich benzyl position and an electron-deficient benzyl position, the electron-rich benzyl position is selectively aminated, and in amination reactions to secondary and tertiary benzyl positions, amination proceeds in a secondary position regioselectively. According to the results of deuterium experiments, the authors suggest that the rate-limiting step in this reaction is the C–H bond cleavage step. Recently, in addition to these C–H amination reactions, Pérez’s group has also reported Si–H amination reactions of silane compounds.

90Transimination reactions have been investigated previously, and a variety of new methods have been reported very recently.− Numerous reports on the imination reactions of sulfur atom using the in situ generated iodonium imide species from NH2CO2NH4,− (NH4)2CO3,, and NH3, have recently been published. The generated PhI = NH species could exist for only a short time but has been successfully detected by HRMS. For example, Bull and Luisi reported that the reaction of a tertiary amine compound 231 with PhIO 17, NH2CONH4, and TsOH efficiently produced a quaternary ammonium product 232 in which the NH2 group from NH2CONH4 was attached to the nitrogen atom of the amine (Scheme 85). The reaction is chemoselective and proceeds nitrogen-atom-selectively even if the substrate contains an oxygen atom or double bond. The authors believe that this reaction involves intermediate formation of PhI = NH species in the reaction system.

91Reactions utilizing iminoiodane without the use of metal catalysts are known, and C–H amination and trans-imination reactions have been reported.− Saito and co-workers reported the cycloaddition reaction using iminoiodanes without metal catalysts. This reaction was performed by adding C6F5INTs to an alkyne 233 in the presence of BF3 in nitrile solvent to give the corresponding imidazole 234 (Scheme 86). The authors synthesized a highly electrophilic iminoiodane, C6F5INTs, and found that this reagent has enhanced reactivity in this reaction.

92Reactions using iminoiodanes under light irradiation conditions− or with photocatalysts have recently been reported. For example, Kobayashi and Takemoto reported the amination of various substrates by activation of iminoiodanes under photoirradiation.,,N-Acyliminoiodanes and N-sulfonyliminoiodanes were used as the iodine reagents in the reaction. The N-acyliminoiodanes were previously reported to be unstable compounds, but the authors found that they could be stabilized by introducing a coordinating substituent at the ortho-position, and their structures were confirmed by X-ray crystallography. In the reaction with N-acyliminoiodane, mesitylene 235 reacted with the iodine(III) reagent 236 (n = 1) under photoirradiation at 365 nm to give the corresponding N-acylated compound 237 (n = 1) in 77% yield (Scheme 87). This reaction also proceeded with iodine reagents bearing perfluoroalkyl groups of different chain lengths to give the respective products in moderate yields. The reaction proceeds efficiently with anisoles and heteroarenes, including some bioactive compounds as substrates, while reactions with toluene, bromobenzene, and chlorobenzene did not afford the products 237.

μ-Oxo-iodine(III) Compounds

93Numerous representatives of μ-oxo-iodine(III) compounds, which are formed by bridging two hypervalent iodine moieties with oxygen atoms, have been synthesized and structurally investigated. In general, these compounds are more electrophilic and more reactive than their monomeric analogues because of the presence of the bridging oxygen., The general method of their synthesis consists of adding water to a monomeric hypervalent iodine reagent under stirring. Since 2016, several new iodine(III) compounds with μ-oxo structure have been synthesized, and their structures have been determined by X-ray crystallography.,,, Recently, Powers and co-workers have found that crystallization of equal amounts of iodine(III) compounds 238 and 239 from a TFE-MeCN mixture yielded yellow crystals of μ-oxo-iodine(III) compound 240 with a tetrameric structure confirmed by X-ray crystallography (Scheme 88). This structure is formed by the elimination of water from dimer 241, which is initially formed by condensation of 238 and 239. The formation of 241 was confirmed by mass spectrometric analysis.

94Deng’s group has successfully synthesized μ-oxo-iodine(III) compounds with a nitrooxy group as a ligand, and their structures have been confirmed by X-ray. Two methods for synthesizing these compounds have been reported: (1) the reaction of DIB with nitric acid and (2) the reaction of silver nitrate with ArICl2; both methods yielded the corresponding μ-oxo-iodine(III) compounds in moderate to high yields. The authors have also investigated the reactivity of these compounds and reported that cyclopropyl trimethylsilyl ether 242 reacts with reagent 243 in the presence of a zinc catalyst to afford β-substituted ketones 244 in which the carbon–carbon bond in the original cyclopropane ring was cleaved (Scheme 89). When TEMPO is added as an additive, the yield of the target product is low and the product due to the combination of the substrate and TEMPO is formed. From these results, the authors suggest that the radical species may be involved in this reaction. They also evaluated the reaction mechanism by computational methods. In the reaction using β-ketoesters and β-keto amides as substrates, the corresponding α-nitrooxylated compounds were efficiently obtained.

[Hydroxy(sulfonyloxy)iodo]arenes

95[Hydroxy(sulfonyloxy)iodo]arenes can be easily synthesized by ligand exchange reactions from [bis(acyloxy)iodo]arenes such as DIB and the corresponding sulfonic acid, most commonly, p-toluenesulfonic acid., These reagents are not only efficient oxidants for various substrates− but also useful sulfoxyloxylating agents.− Furthermore, a difunctionalization reaction of iodination-sulfoxyloxylation has recently been reported. The reaction of 2H-indazole 245 and [hydroxyl(tosyloxy)iodo]benzene (HTIB) 246 in acetic acid solvent under heating affords the corresponding disubstituted 2H-indazole compound 247, which is C-4-sulfonyloxylated and C-7-iodinated (Scheme 90). This reaction proceeds with very high regioselectivity, producing products 247 in generally high yields. Similar reactions of iodine(III) reagents with various other sulfonyloxy groups produce respective products in moderate to high yields.

96Intramolecular cyclization reactions of HTIB leading to the formation of carbon-heteroatom− and carbon–carbon bonds, have been reported. For example, Das and co-workers reported that the reaction of exocyclic β-enaminones 248 with HTIB 246 in the presence of AgSbF6 leads to the formation of the corresponding carbazolones 249 via intramolecular carbon–carbon bond formation (Scheme 91). In the reaction of an exocyclic β-enaminone with 2-aminopyridine as a substituent, an intramolecular carbon-heteroatom bond formation occurs to yield the corresponding imidazo[1,2-a]pyridine. The authors suggest that the rate-limiting step in this reaction is not the aromatic C–H bond cleavage because the deuterium labeling experiments did not reveal any significant kinetic isotope effects. The presence of AgSbF6 is important because the generated iodonium salt 250 with the hexafluoroantimonate counterion acts as a photoinitiator and initiates a free radical reaction via the radical-cation pathway.

97Szpilman’s group has reported the reaction of various substrates with enolonium species generated from mixing silyl enol ethers with HTIB reagents.− For example, silyl enol ether 251 reacts with HTIB 246 in the presence of BF3·Et2O to form enolonium species 252, and then an aromatic compound 253 was added to the reaction to give the corresponding α-arylated ketone 254 (Scheme 92). When one more molecule of silyl enol ether was added instead of the aromatic compound, the corresponding 1,4-diketone was obtained. The authors confirmed the presence of enolonium species formed in this reaction by NMR studies. The same group also reported that the reaction of vinyl azide as the starting material instead of silyl enol ether with HTIB leads to the formation of an analogue of the enolonium species, the azide-enolonium species, which reacts with a nucleophile to give the corresponding α-keto compound.

[Cyano(trifluoromethylsulfonyloxy)iodo]arenes

98[Cyano(trifluoromethylsulfonyloxy)iodo]benzene, PhI(CN)OTf, can be conveniently synthesized by reacting iodosylbenzene or DIB with TMSOTf and TMSCN at low temperature., This reagent was originally reported more than 30 years ago, but its structure was not reliably established. Recently, Dutton and co-workers have revealed its X-ray structure. In particular, the authors found that the I–O bond distance in PhI(CN)OTf is longer than that of the known partially ionic PhI(OAc)OTf. In addition, 19F NMR studies indicated that the triflate signal in this compound is close to the signal of triflate anion, suggesting that PhI(CN)OTf is an ionic compound.

99ArI(CN)OTf reagents are commonly used in the synthesis of various iodonium salts., For example, Hinkle and Pike have reported the cyclization reaction of propargylic alcohols 255 with ArI(CN)OTf, leading to the corresponding naphthyl(aryl)iodonium thiflates 256 in low to good yields (Scheme 93). The authors found from X-ray structural analysis that the hydroxyl group of the fragment R in product 256 is coordinated to the iodine center.

100[Cyano(trifluoromethylsulfonyloxy)iodo]arenes can also be used as cyano-trifluorosulfonyloxylating reagents. Studer’s group has reported that the reaction of alkynes 257 with 3,5-(CF3)2C6H3I(CN)OTf in the presence of iron catalyst can regioselectively afford cyano-triflated products 258 in low to good yields (Scheme 94). These reactions are synthetically useful because they can convert disubstituted alkynes to tetrasubstituted alkenes in one step, and the OTf moiety of the obtained products can be further converted by appropriate treatment.

[Bis(sulfonyloxy)iodo]arenes

101The existence of [bis(sulfonyloxy)iodo]arenes was suggested long ago; however, their structures were not confirmed because of the high reactivity and low stability of these compounds., In particular, the generation of PhI(OTf)2 in situ has been utilized in many papers, but no identification data was provided., Recently, Dutton and co-workers have reported the first successful preparation of p-NO2C6H4I(OTf)2259 from p-NO2C6H4IF25 and 2 equiv of TMSOTf (Scheme 95), and its structure was established by X-ray crystallography. The length of the I–O bond was found to be shorter than that of the reported I-OTf of PhI(OAc)OTf. The authors also found that p-NO2C6H4I(OTf)2259 peaks at a downfield compared to PhI(OAc)(OTf) in the fluorine NMR, suggesting that the I–O bond of p-NO2C6H4I(OTf)2259 is more associative than that of PhI(OAc)(OTf). The compound was highly unstable and decomposed at room temperature, but not under a nitrogen atmosphere at 150 K.

102The same authors have found that the reaction of compound 259 with triphenylmethane 260 yields diaryliodonium triflate 261 in 75% yield (Scheme 96). The control reaction using PhI(OAc)(OTf) instead of 259 did not proceed, indicating the higher reactivity of p-NO2C6H4I(OTf)2259. According to NMR studies, the reaction of compound 259 with cycloheptatriene yields tropylium triflate and the reaction with adamantane gives adamantyl triflate. Furthermore, the reaction of 259 with 1-fluoroadamantane affords p-NO2C6H4I(F)(OTf). From this result, the authors also suggested that compound 259 can act as a Lewis acid.

Iodine(III) Compounds with Trifluoromethyl Ligand

103Acyclic hypervalent iodine compounds with trifluoromethyl groups as ligands are usually unstable at room temperature. The formation of [PhICF3]+-species in solution was confirmed by mass spectrometry, and X-ray structures of pseudocyclic trifluoromethyl-substituted iodanes were previously reported. More recently, in 2018, Wang and co-workers reported the preparation of PhI(CF3)Cl in high yields by adding TMSCF3 to PIFA and treating with NaCl. X-ray structural data indicated a significant ionic character of the I–Cl bond in this compound. This compound can work as a CF3-introducing reagent for various organic substrates.− For example, PhI(CF3)Cl 262 reacts with aromatic isocyanides 263, forming trifluoromethylation and cyclization products 264 in good yields (Scheme 97).

104It has been reported that this reagent can transfer CF3 to a carbon atom as well as to a nitrogen atom. For example, the reaction of PhI(CF3)Cl 262 with nitriles 265 and a nitrogen nucleophile leads to N-trifluoromethylation and amination of the nitrile to give the corresponding amidine products 266 (Scheme 98).N-Heterocycles as well as cyclic and acyclic amines can be used as nitrogen-based nucleophiles in this reaction. Other than nitrogen nucleophiles, alcohols and thiols can also be used as nucleophiles; in this case, the corresponding imidate and thioimidate products are obtained. It was suggested that these reactions involve initial interaction of nitrile 265 with the iodine reagent to form N-CF3 nitrilium ions 267, followed by the reaction of a nucleophile to convert it to the final product. It has been recently reported that when methylene isocyanides are used as nucleophiles, the trifluoromethylation of the nitrile is followed by a cyclization reaction to yield the corresponding N-CF3 imidazoles.

105PhI(CF3)Cl can also be used for the addition of trifluoromethyl groups to alkynes and alkenes. For example, it has been reported that the reaction with alkynes 268 with PhI(CF3)Cl 262 in the presence of NaH leads to the formation of alkenes 269 with syn addition of hydrogen and a trifluoromethyl group (Scheme 99). In the presence of TEMPO this reaction did not yield alkenes 269, which suggests that radicals are involved in the mechanism. Deuterium experiment indicated that the hydrogen atom for the conversion of alkynes to alkenes comes from DMF as the reaction solvent.

106Reactions utilizing perfluoroalkyl-substituted iodanes have also been reported. For example, Studer and co-workers reported that perfluoropropyl-substituted hypervalent iodine reagent 271 reacts with aromatic alkyne 270 in the presence of a copper catalyst to give alkene 272 as a result of anti-addition (Scheme 100). A similar reaction can also be efficiently performed with iodine reagents having perfluorohexyl or perfluorooctyl group as a ligand. The authors sugested that this reaction proceeds via initial generation of perfluoroalkyl radical from the iodine reagent and copper catalyst.

Iodine(III) Compounds with Diazomethyl Ligand

107Hypervalent iodine compounds with a diazomethyl group as the ligand were originally synthesized nearly 30 years ago, and their structure was investigated by X-ray. These compounds can be used as reagents for transfer of the diazomethyl group to various substrates. For example, Singh and co-workers reported that the reaction of carbohydrazides 273 with reagent 274 under basic conditions yields diazirine compounds 275 (Scheme 101). Aromatic and aliphatic carbohydrazides can be used as substrates in this reaction. The reaction also proceeds with iodine reagents having ester moieties with various substituents. The authors suggested that the nitrogen atom of the carbohydrazide 273 initially reacts with reagent 274 to yield intermediate product 276 in which the diazomethyl group is transferred to the nitrogen atom, followed by intramolecular cyclization and oxidation to give the final product 275. In addition to this reaction, transfer reactions of the diazomethyl group to nitrogen atom with various substituents have also been reported., Furthermore, transfer reactions to sulfur− and phosphorus atoms are also known.

108The transfer reaction of the diazomethyl group to the carbon atom has also been reported. Suero and co-workers reported that reactions of silyl enol ethers 277 with reagent 274 under basic conditions afford β-diazocarbonyl compounds 278 (Scheme 102). They found that the reaction proceeds even when natural products and pharmaceuticals were used as substrates. The obtained β-diazocarbonyl compounds undergo stereoselective intramolecular cyclization using a rhodium catalyst to selectively afford 1,3-C–H-inserted cyclized compounds.

109Li and co-workers have also reported the reaction of aromatic tertiary amines 279 with reagent 274 to introduce the diazomethyl group at the ortho-position of the nitrogen (Scheme 103). The resulting products 280 can be converted to the corresponding indole compounds using a rhodium catalyst. The authors suggest that the diazomethyl radical species are generated in this reaction via the formation of an EDA complex between the amine and the iodine reagent. A method for generating diazomethyl radical species with a photocatalyst and iodine(III) reagent under LED irradiation is known, and reactions using these conditions have been reported.

Iodonium Ylides

110Iodonium ylides are carbon analogues of iodonium imides with the carbon atom bonded to the iodine atom., Electron-withdrawing groups such as carbonyl and sulfonyl are usually used as the stabilizing substituents. Iodonium ylides can be synthesized by reacting DIB with a diketone or disulfonyl compound under basic conditions. Recently, Yoshino and Matsunaga reported a procedure in which aryl tin or germanium compounds are reacted with I(CO2CF3)3 to generate PIFA species in the reaction system, followed by the addition of a Meldrum’s acid derivative to produce the corresponding ylide. The same group also reported the synthesis of ylides using iodine triacetate. Structures of several new ylides were investigated by X-ray diffraction studies.− The negatively charged carbon ligands in ylides in general have low nucleophilicity; however, they may act as nucleophiles toward highly electrophilic substrates. Numerous reactions involving the carbon ligand of iodonium ylide have been well investigated, including cyclopropanation,− spirocyclization,− and ylide transfer reactions., In recent years, heterocyclic ring annulation reactions utilizing iodonium ylides and various substrates have been reported. For example, Gao and Li reported a [3 + 3] cyclization reaction using iodonium ylide 281 and enaminone 282 in the presence of rhodium and silver catalyst, resulting in the corresponding isocoumarin products 283 (Scheme 104). Interestingly, this reaction does not proceed with acyclic iodonium ylides. The authors have suggested that the transition state in this reaction involves a C–H cleavage based on deuteration experiments. Similar reactions leading to isocoumarins have been reported by other groups.− Hung and Yu reported that when ruthenium catalyst was used instead of rhodium catalyst in a similar reaction, a [3 + 2] cyclization occurs to afford the corresponding 3a,7a-dihydroxyhexahydro-4H-indol-4-one. Heterocyclic ring annulation reactions utilizing various substrates and iodonium ylides and resulting in [3 + 3],− [3 + 2],− [4 + 1], and [4 + 2],− cyclizations have also been reported.

111While most of these reactions require transition metal catalysts, several publications report heterocyclic synthesis using single electron transfer methodology that does not require transition metal catalysts.− For example, it has been reported that the reaction of acyclic aromatic tertiary amines 284 with iodonium ylide 285 in the presence of visible light irradiation proceeds as the [4 + 1] cyclization to give the corresponding indoline derivatives 286 (Scheme 105). It is also known that when cyclic aromatic tertiary amine compounds were used, N-phenylpyrrolidines could be obtained. In these reactions, the addition of TEMPO does not yield the desired product, while the addition of CCl4 yields a chlorinated compound derived from CCl4, indicating that radicals are involved in the reaction. The authors hypothesize that EDA complexes are formed with iodine(III) and amine reagents in the early stages of the reaction, and these complexes induce single-electron transfer under visible light. As well as cyclization reactions, such reactions using single-electron transfer reactions have also been used in three-component condensation reactions.,

112The insertion of iodonium ylide carbon ligands into C–H bonds has been investigated previously, and several new reports have been published recently.− Jiang and Liu reported that the reaction of a pyridine compounds 287 with an inactive C(sp3)–H bond with a cyclic iodonium ylide 288 in the presence of rhodium and silver catalysts gives products 289 in which the ligand of the iodonium ylide is inserted into the C(sp3)–H bond (Scheme 106). The obtained products could be further converted into various derivatives under appropriate conditions. The authors found that the reaction of 2-(tert-butyl)pyridine with rhodium and silver catalysts in the absence of iodonium ylide produced a cyclic pyridine-rhodium complex compound 290. The reaction of the obtained complex 290 with iodonium ylide 288 gave the desired product, implying that the pyridine-rhodium complex is an important key intermediate in the reaction.

113Several reactions based on the generation and utilization of iodonium ylides in situ have been reported.− Ylide species can be generated by reacting an aliphatic monovalent iodine compound with a diazo compound. Tambar’s group has reported sigmatropic rearrangement reactions using this approach. Addition of tert-butyl α-diazo ester 291 to aryl-substituted allylic iodides 292 in the presence of copper catalysts leads to a [2,3]-sigmatropic rearrangement affording the corresponding terminal alkene products 293 with high regioselectivity (Scheme 107). This reaction proceeds efficiently even with polysubstituted allyl iodides.

114The reactions of iodonium ylides resulting in nucleophilic substitution of the iodonium moiety in an aromatic ring have been reported. In particular, iodonium ylides are commonly used to introduce fluorine-18 radiolabeling into unactivated aromatic rings.,, In recent years, numerous syntheses of iodonium ylides with various substituents in the aromatic ring followed by fluorine-18 radiolabeling on the aromatic ring have been reported.− For example, Li and Cai reported the synthesis and radiofluorination reaction of iodonium ylide 294 to give fluorinated product 295 with a radiolabeled ortho-position (Scheme 108). Reaction with iodonium ylide having an alkoxy group in the para-position also yields compounds with 18F in the para-position. Product 295 can be used as a radioactive tracer suitable for medical imaging of 11β -HSD1 in the primate brain. Several similar reactions leading to the functionalization of the aromatic ring of iodonium ylides have been reported.−

Iodonium Salts

115Iodonium salts are generally defined as hypervalent iodine(III) compounds with two carbon ligands, and their chemistry has been summarized in numerous review articles.,,,,,, The most typical reactions of iodonium salts result in a transfer of the carbon ligand to various nucleophilic organic substrates. Recent examples of the reactions of iodonium salts bearing alkynyl, alkenyl, alkyl, and aryl groups as the ligands are discussed in this section.

116Alkynyliodonium salts can be conveniently synthesized by ligand exchange reactions between alkynyltin compounds and hypervalent iodine(III) reagents. Reactions of alkynyliodonium salts with various nucleophiles lead to a transfer of the alkynyl ligand yielding the corresponding substituted alkynes.− The C–H bond insertion reactions using alkynyliodonium salts are also known. For example, Kalek and co-workers reported that the reaction of aldehydes 296 with alkynyliodonium salts 297 in the presence of an NHC catalyst yields ynones 298 in which the C–H bond of the aldehyde is replaced by the alkynyl group (Scheme 109). Based on 13C-labeling experiments and DFT calculations, the authors suggest that the alkynyl group insertion into the C–H bond of the aldehyde proceeds by direct substitution of iodine via a Breslow intermediate that occurs at the α-acetylenic carbon.

117Recent studies have demonstrated that alkynyliodonium salts can be used for the generation of diatomic carbon (C2). Miyamoto and Uchiyama reported that upon treatment of alkynyliodonium salt 299 with TBAF in the presence of 9,10-dihydroanthracene 300, C2 is generated and trapped to form anthracene 301 and acetylene 302 (Scheme 110). They also reported that nanocarbons such as graphite, carbon nanotubes, and C60 can be produced by reacting alkynyliodonium salt 299 with a source of fluoride anion. The mechanism of C2 formation has been investigated by computational chemistry.− Recently, a reaction utilizing this mehod of C2 generation was reported by Saito’s group. They reported that the reaction of alkynyl iodonium triflate 303 with N-(acyloxy)sulfonamide 304 under basic conditions gave the corresponding N-(acyloxy)-N-alkynylamide 305 (Scheme 111). The authors have also found that, in the presence of TEMPO or galvinoxyl, product 305 is not formed, which supports the reaction mechanism involving C2 reactive species.

118Vinyliodonium salts are useful reagents for vinyl group transfer. Recently, a convenient synthesis of vinyliodonium salts by reactions of alkynes with iodine(III) reagents such as DIB or PhIO has been reported.,, The preparation of vinyliodonium salts from alkynyliodonium salts by addition reaction has also been reported., Vinyliodonium salts can transfer the vinyl group from iodine to carbon atoms and various heteroatoms.,− It has also been reported that these salts can be used for the transfer reactions to radioactive atoms., Gao and co-workers reported the vinyl group transfer reaction to oxygen atoms of arylhydroxylamines. The reaction of arylhydroxylamines 306 with vinyliodonium salt 307 under basic conditions and in the presence of a copper catalyst affords the corresponding indoles 308 (Scheme 112). The authors suggest that the reaction proceeds by the vinylation to oxygen atoms of arylhydroxylamines to give O-vinyl-N-arylhydroxylamines 309, followed by several steps involving [3,3]-sigmatropic rearrangements leading to final product. The resulting compounds 308 can be converted to other indole derivatives by appropriate treatment. In addition to the vinyl group transfer reactions to various atoms, vinyl group insertion reactions into C–H bonds have also been reported.−

119It has been reported that vinyliodonium salts can be used for cyclization reactions as well as the addition of vinyl groups to substrates. For example, Stirling and Novák reported an efficient two-step synthesis of vinyliodonium salts from vinyl iodides and the aziridination reaction using them. In this reaction, reagent 310 and an amine 311 are combined under basic conditions to give the corresponding aziridine 312 (Scheme 113). The authors have also proposed the reaction mechanism. The suggested mechanism involves initial nucleophilic addition of amine to the β carbon of the vinyl moiety, followed by cyclization to the aziridine ring.

120Several representatives of alkyliodonium salts stabilized by electron-withdrawing substituents on the alkyl group were previously known, and several new such compounds have been synthesized and investigated recently. Various reactions of alkyliodonium salts have been studied, including the transfer of alkyl groups to various heteroatoms− and the insertion of alkyl groups into C–H bonds.− For example, Stirling and Novák reported the synthesis of a new alkyliodonium compound 313 from 3-chloro-1,1,1,2-tetrafluoro-2-iodopropane via a dyotropic rearrangement. and its structure was established by X-ray crystallography. The authors have also found that the reaction of compound 313 with anilines 314 under basic conditions gave the corresponding alkylanilines 315 (Scheme 114). In addition to anilines, the authors have also reported N-alkylation reactions of heterocyclic compounds and C-alkylation reactions of indoles.

121Diaryliodonium salts represent one of the most common classes of hypervalent iodine compounds with many practical uses. A broad variety of symmetric, nonsymmetric, and heterocyclic diaryliodonium compounds have been synthesized and utilized as reagents in organic synthesis.,,,,,− Diaryliodinium salts with various functional groups have been recently synthesized using two main approaches: (1) the reaction of aromatic compounds with hypervalent iodine(III) reagents or (2) the in situ oxidation of aryl iodides in the presence of aromatic compounds.− Various counteranions have been introduced in the structure of diaryliodinium salts.,− Structures of numerous new diaryliodinium salts have been established by X-ray crystallography. The reactivity of these compounds as Lewis acids depending on the substituents in the aromatic ring has been investigated., Diaryliodonium salts are widely used as reagents for the arylation of nucleophilic carbon− or heteroatoms− in various substrates. The reactions of diaryliodonium salts with the corresponding nucleophiles are often used for the introduction of a radioactive label into an aromatic ring, such as the introduction of radioactive fluorine,− bromine, and carbon.

122Several rearrangement reactions resulting in the transfer of an aryl group in diaryliodonium species to a heteroatom at the ortho-position of the second aryl substituent have recently been reported.− Olofsson and co-workers have reported that heating of a diaryliodonium salts 316 bearing a cyclic amino group in the ortho-position, followed by the addition of piperidine as a nucleophile under basic conditions, affords the corresponding anilines 317 (Scheme 115). The initial product of this reaction, quaternary ammonium salt 318 resulting from the rearrangement of iodonium salt 316, can be isolated. Ammonium salts 318 can be efficiently converted to the final aniline products by adding piperidine or other nitrogen, halogen, and oxygen nucleophiles.

123Diaryliodonium salts are commonly used as benzyne or aryne precursors. Recently, numerous examples of such reactions have been reported.,,− Kitamura and his group have reported the synthesis and reactions of diaryliodonium salt that can consequently generate benzyne species at the 1- and 4-positions. For example, the reaction of [2,5-bis(trimethylsilyl)-4-(trifloxy)phenyl](phenyl)iodonium triflate 319 in the presence of CsF with 2,5-dimethylfuran as a first arynophile and tetraphenylcyclopentadienone as a second arynophile leads to a double cycloaddition reaction to give the corresponding product 320 in high yield (Scheme 116). The same group has also succeeded in synthesizing diaryliodonium salt, which can generate benzyne species at both the 1- and 3-positions, and reported the double cycloaddition reaction using this salt.

Cyclic Iodine(III) Compounds as Reagents

124Cyclic hypervalent iodine compounds in general have higher thermal stability and modified reactivity compared to their acyclic analogues. The high thermal stability and lower reactivity of these compounds is explained by the link between apical and equatorial ligands at the iodine center, which restricts pseudorotation and reductive elimination of the iodoarene fragment., The vast majority of practically important cyclic hypervalent iodine reagents are based on the heterocyclic systems of benziodoxole or benziodazole. In recent years, various iodine-substituted benziodoxole derivatives have been prepared and utilized as reagents for transfer of the substituent on hypervalent iodine to organic substrate. The chemistry and synthetic applications of benziodoxoles and other hypervalent iodine heterocycles have been summarized in numerous recent reviews.,,,,

Fluorobenziodoxoles and Fluorobenziodazoles

125Cyclic hypervalent iodine compounds with fluorine atoms as ligands belong to a relatively new class of iodine reagents originally synthesized about 10 years ago. A new synthesis of fluorobenziodoxoles from the corresponding aryl iodides and AgF2 was recently reported. Fluorobenziodoxoles are useful fluorinating reagents, similar to acyclic difluoroiodoarenes. In particular, numerous examples of fluorocyclizations of olefinic substrates using fluorobenziodoxoles have been reported.− Li and Lu have found that the reaction of fluorobenziodoxole 322 with an unsaturated carbamate 321 leads to an intramolecular fluorocyclization yielding fluorinated oxazolidin-2-ones 323 (Scheme 117). The addition of TEMPO to the reaction reduces the yield of the products 323, and the addition of BHT yields a BHT-substituted products, which suggest that radical species are involved in the reaction mechanism. Fluorobenziodoxole with a radioactive fluorine ligand can also be used in this reaction to introduce radioactive fluorine atom into the product.

126When a diazocarbonyl compound, instead of an olefin, is used as a substrate in the reaction with a hypervalent iodine reagent in the presence of an oxygen nucleophile, an intermolecular oxyfluorination reaction proceeds, yielding the corresponding fluorinated product.− It has also been reported that, in the reaction of diazonium salts with a catalytic amount of iodine reagent and catalytic amount of BF3·Et2O, Baltz-Schemann reaction proceeds efficiently and the corresponding aromatic fluorinated compounds are obtained. Several other fluorination reactions of hypervalent iodine fluorides have been reported., For example, Zhang and co-workers reported that the reaction of cyclopropane derivative 324 with fluorobenziodazole 325 in the presence of BF3·Et2O leads to a ring-expanding fluorination reaction, resulting in the corresponding six-membered cyclic products 326 (Scheme 118). The authors suggested that the active iodine species in this reaction is the complex of the iodine reagent and BF3, which was observed by NMR and mass spectrometry. The reaction mechanism was proposed using DFT calculations.

127Several reactions of fluorobenziodoxoles resulting in addition–elimination of fluorine have been reported.,, For example, Gulder and co-workers reported a reaction in which the addition of fluorobenziodoxole 322 in the presence of a nucleophile to 2-pyridyl ketones 327 leads to α-functionalized pyridyl ketone 328 (Scheme 119). In this reaction, the α-position of the pyridyl ketone is first fluorinated, followed by a substitution reaction with a nucleophile to obtain the final product. In the absence of a nucleophile, the reaction yields the product of α-fluorination of the pyridyl ketone. The presence of the nitrogen atom in position 2 of the pyridyl ketone is essential; the product cannot be obtained by using a ketone substrate with a benzene ring instead of a pyridine ring or an isomer with a different position of nitrogen of the pyridine ring.

Chlorobenziodoxoles and Chlorobenziodazoles

128Chlorobenziodoxoles, cyclic iodine(III) derivatives with a chlorine atom ligand, are important chlorinating reagents for various organic substrates. Several new chlorination reactions using chlorobenziodoxoles have been reported recently.− Murphy and co-workers reported that the reaction of aromatic allenes 329 with chlorobenziodoxole 330 yields products of dichlorination of the terminal double bond 331 with predominant (Z)-selectivity (Scheme 120). In the reaction of an aromatic allene with an alkyl group R1 at the α-position of the allene, a mixture of dichlorinated and monochlorinated products is formed. A similar reaction of an allene with (dichloroiodo)benzene is not selective, leading to several isomers of dichlorinated products.

129Chlorobenziodoxoles can also be used as selective oxidants of organic substrates.− For example, the reaction of alkynes 332 with chlorobenziodoxole 333 and sodium sulfonates 334 efficiently yields 1,2-disulfonylethenes 335 with high (E)-selectivity (Scheme 121). The authors believe that radicals are involved in this reaction because in the presence of TEMPO product 335 is not formed. They also assume that the initial products of ligand exchange between chlorobenziodoxole with sodium arylsulfinates are the active species in this reaction, as confirmed by ESI-MS spectrometry.

130Du and co-workers have found that the reaction of chlorobenziodazole 336 with silver cyanate in water and chloroform as cosolvents formed μ-oxo compound 337 (Scheme 122). The authors have also reported that, in the absence of water, compound 338 with isocyanate ligand was obtained. Both structures were determined by X-ray crystallography.

Alkoxybenziodoxoles

131The acyclic hypervalent iodine compounds with alkoxy group ligands are relatively unstable and difficult to handle, whereas the cyclic derivatives, alkoxybenziodoxoles, are stable compounds. Alkoxybenziodoxoles can be prepared by a ligand exchange reaction of hydroxy- or acetoxybenziodoxoles with the corresponding alcohol, and their structure has been established by X-ray analysis., Recently, these compounds have been used as the reagents for C–H oxidation reactions.,,− For example, Chen and co-workers reported that sulfides 339 react with methoxybenziodoxole 340 in the presence of a photocatalyst under LED irradiation to form 2-iodobenzoic esters 341 via C–H acyloxylation reaction (Scheme 123). This reaction proceeds efficiently not only with aryl- and alkyl-substituted substrates 339 but also with sulfur compounds with amino acid fragments as substituents. The C–H bond cleavage is the rate-determining step in this reaction, as confirmed by the reaction of deuterium-substituted substrate. The reaction most likely has a radical mechanism as supported by the experiments in the presence of TEMPO or BHT.

132Wallentin and co-workers prepared numerous alkoxybenziodoxoles by ligand exchange reactions between various alcohols and acetoxybenziodoxole, and reported C–H oxidation with these reagents. When these alkoxybenziodoxoles 342 were treated with blue LED irradiation in the presence of a photocatalyst, an intramolecular cyclization reaction proceeded, resulting in the chromane products 343 (Scheme 124). In this reaction, the photocatalytic one-electron reduction of compound 342 generates the corresponding alkoxy radicals, followed by radical cyclization to yield the final products 343 along with 2-iodobenzoic acid as a by-product. This radical cyclization proceeds by competitive 1,5- and 1,6-addition reactions, resulting in the formation of two structural isomers.

133A C–H alkylation reaction of heteroaromatic rings using in situ generated alkoxybenziodoxole has been reported. In this reaction, cyclic acetoxybenziodoxole 344 reacts with various alcohols 345 and 4-chloroquinoline 346 in the presence of a photocatalyst and under irradiation with compact fluorescent lamps to form products 347 in which the 2-position of the quinoline ring is alkylated (Scheme 125). The reaction is also applicable to the substrates derived from natural products. The authors were able to isolate the initially formed alkoxybenziodoxole and demonstrated that it can be directly used in this reaction.

Acyloxybenziodoxoles

134Acyloxybenziodoxoles are usually prepared by ligand exchange reactions between hydroxybenziodoxoles or acetoxybenziodoxoles and carboxylic acids, and the structures of several acyloxybenziodoxoles have been determined by X-ray crystallography., Preparation of numerous acyloxybenziodoxoles using various carboxylic acids has been reported.− Acyloxybenziodoxoles can be formed in situ in the reaction system by ligand exchange reactions and used for the generation of acyloxy radicals via radical cleavage of the I–OCOR bond under reaction conditions. Further decarboxylation of the acyloxy radicals can produce alkyl radicals. The radical species generated in this process then undergoes various inter- and intramolecular reactions. As an example of the intermolecular reaction, Cramail and Landais reported that acetoxybenziodoxole 344 reacts with oxamic acid 348 and alcohol 349 under blue LED irradiation in the presence of a photocatalyst, leading to a decarboxylation reaction of oxamic acid and forming urethane products 350 (Scheme 126). It was reported that the addition of amines instead of alcohols yields the corresponding ureas. The proposed mechanism of this reaction involves initial formation of the carbamoyl radicals followed by their reaction with alcohols or amines to give final products. This mechanism was confirmed by additional experiments with TEMPO additives. The same group reported that when 4-methylquinoline 351 was used instead of alcohol in this reaction, products 352 with a carbamoyl group introduced at the 2-position were obtained. Other than 4-methylquinoline heterocycles can be used in this reaction to give the corresponding products regioselectively and in high yield. Recently, the same group has reported an example of a similar reaction using Os(bptpy)2(PF6)2 instead of 4-CzIPN as a photocatalyst under near-infrared light irradiation.

135Several intra-, and intermolecular reactions− have been reported using one-electron transfer process between excited photocatalyst and acetoxybenziodoxole. An intramolecular cyclization occurs in the reaction of acetoxybenziodoxole 344 with cyclic alcohols 353 bearing an anilide moiety in the presence of [Ru(bpy)3Cl2·6H2O] as a photocatalyst under blue LED irradiation and leading to the medium-sized ring lactams 354 (Scheme 127). This reaction also proceeds with heterocycle-substituted alcohols as substrates, resulting in the corresponding lactam products. Additional experiments in the presence of TEMPO suggested that this reaction proceeds via amidyl radicals. As an example of an intermolecular reaction utilizing a similar combination of a photocatalyst and acetoxybenziodoxole, a reaction of primary alkylborates 355 with TsCN 356 leading to cyanoalkanes 357 was reported (Scheme 128). It was also reported that the reaction of alkylborates with pyridine-N-oxides instead of TsCN yields alkylated pyridine-N-oxides.

136Acyloxybenziodoxoles and their derivatives have also been used as coupling reagents for various substrates.−

Azidobenziodoxoles and Derivatives

137Preparation, structure, and reactivity of azidobenziodoxoles were originally reported about 30 years ago., The chemistry of these compounds was recently summarized in several specialized reviews.,, These compounds have been used as efficient reagents for transfer of the azido groups to various organic substrates., Some azidobenziodoxoles have low thermal stability and can be sensitive to friction and shock. To improve the stability of these reagents, substituents can be introduced into the aromatic ring, or the iodoxole ring can be modified with various functional groups. The stability of azidobenziodoxoles has also been investigated by computational analysis., Typical reactions of azidobenziodoxoles include the following: azide addition to unsaturated compounds,− azidation of C–H bonds,− and application as HAT reagents utilizing the generated azido radical species.− Waser and co-workers reported that reactions of alkenes 358 and alkynyl borates 359 with azidobenziodazole 360 under blue light irradiation in the presence of a photocatalyst yield products 361 in which the azido and the alkynyl groups are regioselectively bonded to the alkene (Scheme 129). Proposed mechanism of this reaction includes initial generation of azido radicals by interation of the photocatalyst excited by blue light reacting with the iodine reagent, followed by regioselective addition to the olefin. When diphenyl phosphate is used in place of the alkyne, the corresponding product is obtained in moderate yield. The authors also noted that the azide moiety of the obtained compound can be efficiently converted to an amine by reduction.

138Azidobenziodoxoles can also be used in intramolecular azidation-cyclization reactions. For example, Cao and Deng reported that the reaction of tryptamines 362 with azidobenziodoxolone 363 in the presence of a copper catalyst and a catalytic amount of a chiral ligand leads to a dearomatic asymmetric azidation-cyclization reaction to afford the corresponding tricyclic products 364 with high enantioselectively (Scheme 130). The authors believe that azide-Cu intermediates are initially formed from the iodine reagent and copper catalyst, and further reaction proceeds via radical addition of active azido radicals generated from these intermediates to tryptophan. Addition of various radical scavengers to the reaction suppressed the formation of products 364, confirming the involvement of radical species in the reaction mechanism.

139Selective azidation of the alkyl group attached to the 2-position of the indole ring using azidobenziodoxoles has been reported. For example, the reaction of indole derivatives 365 with azidobenziodoxole 363 in the presence of a copper(I) catalyst provides products 366 that are selectively azidated in the alkyl group (Scheme 131). A similar azidation occurs with tetrahydrocarbazole as a substrate.

140The azido radical species produced from azidobenziodoxole can also be used in hydrogen abstraction reactions of various substrates. For example, Chen and Wang reported that the reaction of compound 367 containing a tertiary alkyl group as a substrate with azidobenziodoxole 363 in a chloroform-water mixture under visible light irradiation yields product 368 in which the tertiary C–H is chlorinated (Scheme 132). This reaction proceeds even when secondary alkyl groups are used as substrates, but the selectivity is slightly reduced. Bromoform can be used instead of chloroform to obtain the corresponding brominated compounds. In this reaction, light irradiation generates active azido radicals, which selectively abstract hydrogen from the substrate, producing carbon radical species, followed by chlorine or bromine abstraction from chloroform or bromoform to give final products.

Amido-, Amino-, and Iminobenziodoxoles

141Numerous cyclic hypervalent iodine compounds with the amino, amido, or similar nitrogen functional groups as ligands have been synthesized, and their structures have been established by X-ray crystallography.,− Many of these compounds can be used as efficient nitrogen functional group transfer reagents to various substrates. For example, Bolm and co-workers reported that the reaction of styrenes 369 with 1-sulfoximidoyl-1,2-benziodoxoles 370 under blue LED irradiation in the presence of Eosin Y as a photocatalyst efficiently gave the bifunctionalized products 371 (Scheme 133). The authors suggest that the hydrogen bonding ability of the phenolic hydroxyl and carboxyl moieties of the photocatalyst Eosin Y influences the intermediates involved in this reaction as well as the stereochemistry of the products. Hydrogen bonding is important in this reaction, and the reactions in the presence of Ru- or Ir-based photocatalysts do not show any significant diastereoselectivity.

142Kiyokawa and Minakata reported several reactions using benziodoxoles with (diarylmethylene)amino groups as ligands.,, For example, in the reaction of styrenes 372 and carboxylic acids 373 with reagents 374 under basic conditions with blue LED irradiation, a bifunctional addition proceeds to give products 375 (Scheme 134). This reaction proceeds via initial formation of diphenyl iminyl radical and ortho-iodobenzoyloxy radical generated from the iodine(III) reagent by blue LED irradiation.

143A reaction involving the combination of a benziodoxole and imido compounds to generate an I–N bonded iodine(III) reagent in situ has been reported. Xue and Chen’s group reported that the reaction of dimethylbenziodoxole 376 with cyclic alcohols 377 and imides 378 in the presence of a copper catalyst, a photocatalyst, and catalytic amounts of ligands under blue LED irradiation gave the corresponding imidoketones 379 (Scheme 135). The authors detected the intermediate alkoxy iodine(III) active species in this reaction formed from dimethylbenziodoxole and alcohols and the iodine(III) species with I–N bonds from dimethylbenziodoxole and amino compounds by 1H NMR. The structure of one of the iodine(III) compounds with an I–N bond has been determined by X-ray crystallography. This reaction is applicable to bioactive molecules with complex skeletons such as cholesterol derivatives and Celecoxib as substrates to obtain the corresponding products. The authors have also investigated the mechanism of this reaction by DET calculations as well as UV–vis and fluorescence quenching experiments.

144Cyclic hypervalent iodine reagents with amino ligands are useful reagents for transfer of the amino group to organic substrates. For example, Liu and Chen reported that the carbazole-substituted benziodoxole 380 reacts with thiophenes 381 in the presence of a copper catalyst, resulting in a regioselective C–H insertion of the carbazole group forming products 382 (Scheme 136). The C–H amination reactions of anilines using aminobenziodoxoles with cyclic amino group ligands, and α-amination to β-ketoesters using aminobenziodoxoles with acyclic aliphatic amine ligands have also been reported.

Trifluoromethylbenziodoxoles and Derivatives

145Trifluoromethylbenziodoxoles and their analogues are cyclic iodine(III) compounds with a trifluoromethyl group as a ligand, which are useful trifluoromethylation reagents that can transfer the trifluoromethyl group to various heteroatoms, unsaturated bonds, and C–H bonds.,, Various trifluoromethyl-substituted cyclic iodine(III) compounds were synthesized, and their structures were investigated by X-ray crystallography.− Trifluoromethylbenziodoxoles or their analogues are commonly used as the reagents for transferring trifluoromethyl group to heteroatoms such as oxygen,− nitrogen, and sulfur− atoms. For example, Togni’s group reported the trifluoromethylation of alcohols using a cyclic iodine(III) reagent derived from 2-iodosufoximine. When alcohols 383 were treated with reagent 384 in the presence of Zn(NTf2)2, the trifluoromethylation reaction proceeds to form the corresponding trifluoromethyl ether 385 (Scheme 137). When 1-trifluoromethyl-1,2-bendiodoxol-3(1H)-one is used in this reaction instead of 384, the reaction does not proceed, suggesting that electron-withdrawing properties of the sulfoximine fragment in reagent 384 is important. If a mixture of primary and secondary alcohols is used in intermolecular competitive reaction, the trifluoromethylation proceeds in favor of the primary alcohol, and in the reactions of substrates with primary and secondary alcohol moieties in the same molecule, the trifluoromethylation of the primary alcohol occurs.

146Reactions of some unsaturated substrates with trifluoromethylbenziodoxoles proceed as cyclization-trifluoromethylation, resulting in various cyclic compounds.− Likewise, the reactions of substrates bearing an isocyanate group lead to the products of cyclization (Scheme 138).,,, Wang and Li reported that the reaction of aromatic isocyanate compounds 386 with 1-trifluoromethyl-1,2-benziodoxole-3(1H)-one 387 gave trifluoromethylated quinolines 388. Studer’s group found that the reaction of biaryl isocyano compounds 389 with reagent 387 under electrochemical reaction conditions produced quinoline products 390. The reaction of α-benzylated tosylmethylisocyanides 391 yields the corresponding 1-trifluoromethylated isoquinoline derivatives 392. Furthermore, it has been reported that the reaction of o-isocyanodiphenylamines 393 as substrates provides trifluoromethylated dibenzodiazepine derivatives 394. In these reactions, trifluoromethyl radical species are generated from the iodine(III) reagent under reaction conditions, which further react with the isocyanate to generate imidoyl radical species, followed by intramolecular cyclization to produce the final products.

147Bifunctionalization reactions of unsaturated compounds with reagent 387 or its analogues in the presence of nucleophilic substrates have been reported. Various reactions proceed by the addition of trifluoromethyl radicals generated from reagent 387 to unsaturated bonds, and the radical species containing nitrogen,− oxygen,,− or carbon− atoms have been utilized as the second radical species for the bifunctionalization reactions of unsaturated bonds. Bifunctionalization reactions of styrene using trifluoromethylbenziodoxoles have been reported (Scheme 139). For example, the reaction of arylhydrazines 395 with reagent 387 and styrene 396 under blue LED irradiation in the presence of rose bengal as a photocatalyst proceeds as aminotrifluoromethylation of styrene, resulting in the efficient formation of the corresponding amines 397. The addition of radical scavengers to this reaction decreased the yield of products 297. The reaction progress stops when blue LED irradiation is stopped, which suggests that the reaction probably does not have a radical chain propagation mechanism. Reactions involving 1,2-oxytrifluoromethylation of styrene have also been reported. The reaction of N-hydroxyphthalimide 398 and styrene 396 with iodine reagent 399 in the presence of vanadium catalyst results in enantioselective 1,2-oxytrifluoromethylation to give the corresponding bifunctionalized product 400. The reaction proceeds enantioselectively for styrenes with various substituents. The enantioselectivity of this reaction has been analyzed by computational methods. Li and Han have also reported that the reaction of styrene 396 with aromatic aldehydes 401 in the presence of an NHC catalyst results in acylfluoroalkylation of styrene to give the corresponding products 402. The reaction proceeds with various aliphatic alkenes as well as styrenes with various substituents. Even indoles and complex biologically active compounds can be used in place of styrene in this reaction.

148The bifunctionalization reactions are also possible for alkyne derivatives.− For example, Liu and co-workers reported that reactions of aryl-substituted alkynes 403 with TMSCN and benziodoxole 399 in the presence of a copper catalyst lead to regioselective bifunctionalization, yielding the corresponding alkene derivatives with atroposelectivity (Scheme 140). A similar reaction proceeds when TMSN3 is used instead of TMSCN to give the corresponding azides. The authors suggest that this reaction has a radical mechanism since adding CBr4 to the reaction competitively yields a bromine adduct, and using a radical clock substrate with a cyclopropyl group opens the ring to give the corresponding allene product. The selectivity of the reaction is also explained by DFT calculations.

149The cyclic iodine(III) reagents with trifluoromethyl ligand can also be used for the trifluoromethyl group insertion into C–H bonds of various substrates.− For example, MacMillan and co-workers reported that the reaction of pyrrolidine 405 with trifluoromethylbenziodoxole 387 under Kessi lamp irradiation in the presence of decatungstate and a copper catalyst led to regioselective trifluoromethylation to C–H, resulting in 3-(trifluoromethyl)pyrrolidine 406 in 66% yield (Scheme 141). The reaction proceeds regioselectively for various aliphatic amines and benzylic position selectively for benzylic substrates. The authors have confirmed the presence of “Cu-CF3” species in various control experiments and suggest that this species may potentially be a catalytic intermediate in the reaction.

150Trifluoromethylation reactions at the C(sp2)–H bonds have also been reported.− For example, it was reported that aniline compounds 407 react with trifluoromethylbenziodoxole 387 in the presence of a catalytic amount of Ni(OH)2 to give products 408 with trifluoromethyl group in the aromatic ring (Scheme 142). This reaction proceeds efficiently with various substituted anilines. Khaskin and co-workers reported that the reaction of 1,3,5-trimethoxybenzene 409 with C2F5-substituted benziodoxole 410 in the presence of nickel catalyst gave fluoroalkylated product 411 in 86% yield. This reaction efficiently proceeds with electron-rich aromatic compounds; however, a decrease in yield is observed for electron-deficient aromatic substrates. In the reactions of C3F7-substituted benziodoxole as the reagent, the analogous fluoroalkylated product was obtained in similar yields.

Cyanobenziodoxoles

151Cyclic iodine compounds with a cyano group as a ligand are used as reagents that can introduce a cyano group into various organic substrates., In contrast with the cyclic iodine reagents, the acyclic hypervalent iodine compounds are not effective cyano group transfer reagents. Reactions utilizing cyclic iodine reagents bearing a cyano group can be used to convert the N–H bond to a N–CN bond,, and the acidic C–H bond to a C–CN bond., Feng and Liu reported that the reaction of the β-ketoester 1-indanone derivatives 412 with cyanobenziodoxole 413 in the presence of a chiral catalyst results in enantioselective α-cyanation to afford the corresponding products 414 (Scheme 143). A similar enantioselective cyanation reaction proceeds with β-ketoamide compounds as the substrates. The reaction does not provide products of cyanation with acyclic β-ketoester or nonaromatic cyclic β-ketoester as the substrates.

152Reactions of carboxylic acids or their derivatives with cyanobenziodoxole 413 proceed as a decarboxylation-cyanation process.− For example, Waser and co-workers reported that the reactions of an aliphatic carboxylic acids 415 with cyanobenziodoxole 413 under blue LED irradiation in the presence of a photocatalyst proceeds to a cyanation reaction via decarboxylation, efficiently yielding the corresponding cyano products 416 (Scheme 144). This reaction does not work effectively with the acyclic hypervalent iodine reagents. The authors suggested that this reaction mechanism involves radicals since the reaction in the presence of TEMPO produces less product, while the reaction with a substrate having a cyclopropylmethyl group produces ring-opened products.

153The TMS group can be substituted by the cyano group using cyclic hypervalent iodine reagents. Yuan and co-workers reported that α-silylated tertiary aliphatic amines 417 react with cyanobenziodoxole under blue LED irradiation to give the corresponding cyano compounds (Scheme 145). The authors propose the formation of an EDA (electron donor–acceptor) complex between the iodine and the amine as a key intermediate in this reaction. The presence of the EDA complex was confirmed by UV–vis spectroscopy. The 1:1 ratio of iodine(III)/amine in this complex was found by the Job’s method.

Cyclic Diaryliodonium Salts

154The chemistry and synthetic applications of cyclic aryliodonium salts were summarized in a comprehensive review. Very recently, a number of various polycyclic diaryliodonium compounds have been synthesized and investigated.,, Similar to the acyclic diaryliodonium salts, these compounds have a relatively high stability. The iodonium atom in cyclic diaryliodonium salts can be substituted with various nucleophiles, forming new heterocyclic or carbocyclic rings, which has been utilized in the synthesis of the corresponding heterocyclic,− triphenylene,− and spirocyclic compounds., Cyclic diaryliodonium salts can also react with various nucleophiles to give the ring-opening products.− Tan and Xu reported that the reaction of cyclic diaryliodonium salt 419 with tellurium powder in the presence of 2-picoline as a base gives dibenzotellurophene 420 in high yield (Scheme 146). Cyclic diaryliodonium salts with various substituents can be used as substrates in this reaction. The authors have also found that tritellurasumanene can be synthesized from the corresponding cyclic diaryliodonium salt by using this methodology.

155Rohde and Hong reported that the reaction of cyclic diaryliodonium salt 419 with unactivated heterocycles 421 under basic conditions yields the corresponding polycyclic heteroarenes 421 (Scheme 147). In this reaction, the corresponding products could be efficiently obtained using substituted cyclic diaryliodonium salts and benzene instead of heterocycles 421. Addition of TEMPO resulted in lower yields of the product, and the TEMPO adduct was detected by ESI-MS, leading the authors to suggest that radicals are involved in the reaction. In a competitive reaction involving a heteroaromatic compound mixed with its deuterated analogue, the kinetic isotope effect is close to 1, indicating that the deprotonation of the C–H of the heteroaromatic ring is not a rate- determining step.

156As an example of ring-opening reactions of cyclic diaryliodonium compounds 423, Wu and Liao reported that the reaction with amines 424 in the presence of a catalytic amount of palladium and a ligand under a carbon monoxide atmosphere leads to the enantioselective double carbonylation, yielding the corresponding ketoamides 425 (Scheme 148). In the reaction using aromatic amines instead of aliphatic amines, the monocarbonylation reaction proceeds and the corresponding amides are selectively produced. The authors evaluated the mechanism of these reactions by DET calculations. Active palladium(IV) species generated by the action of iodonium salt were detected by HRMS and 31P NMR.

157Similar to their acyclic analogues, cyclic diaryliodonium salts can produce benzyne species under basic conditions, which has been utilized in several recent works., Zhang and Wu reported that the reaction of cyclic iodonium salt 419 with phenolic compounds 426 in the presence of cesium carbonate as a base lead to a meta-selective o-arylation reaction, resulting in the efficient formation of the corresponding diaryl ethers 427 (Scheme 149). The same research group has also reported a reaction using tetrabutylammonium halide instead of a phenol compound as a nucleophile, in which a meta-selective halogenation also proceeds, resulting in the corresponding dihalobiaryl products. In the presence of furan instead of phenol or halide, the corresponding cycloadduct was obtained, supporting the generation of benzyne intermediates in this reaction.

Alkynyl- and Alkenylbenziodoxoles

158The chemistry and synthetic applications of alkynyl- and vinylbenziodoxoles were summarized in recent comprehensive reviews.,, Cyclic hypervalent iodine derivatives with alkynyl ligands can be synthesized by ligand exchange reactions of the approporiate cyclic hypervalent iodine reagents with silylated or boronated alkynes. Recently, numerous new alkynyl derivatives of benziodoxole or benziodazole have been synthesized and structurally investigated by X-ray crystallography.− These cyclic alkynyl iodine(III) derivatives have been used in a number of reactions as useful reagents for transfer of the alkynyl group to a variety of substrates.,, In particular, these reagents can be used for alkynylation of unsaturated substrates such as alkenes− and alkynes., Chen and Liu reported that the reaction of aliphatic alkenes 428 with alkynylbenziodoxoles 429 under a carbon monoxide atmosphere in the presence of a catalytic amount of palladium proceeds as alkynylcarbonylation to form the corresponding esters 430 (Scheme 150). The resulting compounds can be converted to a variety of heterocyclic products by appropriate treatment. The same group also reported that hydrogen-alkynation of alkenes can be achieved by a related reaction using (n-hex)3SiH as the hydrogen source instead of carbon monoxide.

159Reaction of diazo compounds 431 with alkynylbenziodoxoles 432 under blue light irradiation proceeds as oxy-alkynylation, yielding propargylic esters 433 (Scheme 151). The authors assume that radicals are not involved in the mechanism of this reaction since the addition of TEMPO or BHT does not decrease the product yield. They suggested that this reaction may involve singlet carbenes generated from diazo compounds under blue LED conditions. It is also known that the oxy-alkynylation of diazo compounds to the corresponding propargylic esters can be achieved by the reaction with alkynylbenziodoxoles in the presence of a copper catalyst., Alcohols or amines can be introduced in this reaction instead of 2-iodobenzoic acid.,

160Alkynylbenziodoxoles have been used as alkynylating reagents toward heteroatoms as well as various C–H bonds.− Furthermore, alkynylation-decarboxylation reactions of carboxylic acids in the presence of photocatalysts have been reported.,− These reactions have been summarized in recent review articles., Recently, Tada and Ito have synthesized cyclic iodine(III) reagents with diyne ligands. They reported that the reaction of reagent 434 with amines 435 in the presence of a copper catalyst and a ligand gave the corresponding diynamides 436 (Scheme 152). The resulting diynamide product can be further converted to ynamides via CuAAC (copper-catalyzed azide–alkyne cycloaddition) by appropriate treatment.

161It has been reported that cyclic alkynyl iodine(III) compounds can be converted to cyclic alkenyl iodine(III) compounds by reaction with various nucleophiles.,− For example, Waser and co-workers reported that the reaction of alkynylbenziodoxoles 437 with sulfonamides 438 under basic conditions proceeds stereoselectively, resulting in Z-alkenylbenziodoxoles 439 (Scheme 153). Phenolic compounds can also be used as nucleophiles in this reaction. The role of the base is to prevent the formation of the ynamide, which is a thermodynamically favorable by-product. In general, cyclic alkenyl iodine(III) compounds can be synthesized by two approaches: (1) by the in situ reaction of 2-iodobenzoic acids with an oxidant and then reacting with an alkene or alkyne followed by base treatment,, or (2) by reacting the cyclic iodine(III) reagents with alkynes.−

162Alkenylbenziodoxoles are used as reagents that can transfer alkenyl groups to various substrates.− For example, Olofsson and co-workers reported that the reaction of alkenylbenziodoxoles 440 with thiols 441 proceeds stereoselectively under basic conditions to give E-alkenylthioethers 442 (Scheme 154). Mercaptothiazoles can also be used as nucleophiles in this reaction.

Pseudocyclic Hypervalent Iodine(III) Reagents

163Hypervalent iodine compounds with appropriate substituents in the ortho-position of the aromatic ring have a pseudocyclic structure due to the intramolecular noncovalent interaction between iodine and the neighboring group. The presence of additional intramolecular coordination at the iodine(III) center leads to a significant improvement of solubility and stability, as well as to modified reactivity of a hypervalent iodine reagent. Synthetic applications of pseudocyclic hypervalent iodine compounds were summarized in a comprehensive review. The coordinating group in the ortho-position of pseudocyclic hypervalent iodine compounds can contain oxygen atoms,,,,,,− such as carbonyl, ether, and hydroxyl groups, or nitrogen-containing functional groups.− Two general methods for the synthesis of common pseudocyclic hypervalent iodine(III) reagents are known. The first method is to add acid to a cyclic hypervalent iodine(III) compound in order to open the ring and create a coordinating functional group. The second method is by the oxidation of iodoarenes with coordinating functional groups in the ortho-position. The structure of numerous pseudocyclic hypervalent iodine compounds has been confirmed by X-ray crystallography.,,,,− For example, the addition of TfOH to hydroxybenziodoxoles 443, followed by the addition of alkynes 444, efficiently synthesizes the corresponding pseudocyclic β-trifluorosulfonyloxy alkenyliodonium salts 445 (Scheme 155). These products can also be obtained by adding Tf2O instead of TfOH. The structure of compounds 445 was determined by X-ray crystallography. The obtained pseudocyclic compounds 445 react with sodium azide in the presence of crown ether by the addition-elimination mechanism with retention of configuration, resulting in the alkenylbenziodoxoles with an azide group at the β-position.

164Wirth and co-workers reported the synthesis of pseudocyclic hypervalent iodine compounds 447 by the oxidation of iodoarenes 446 with a heteroaryl carbonyl group at the ortho-position of the iodine atom (Scheme 156). The structure of these compounds was confirmed by X-ray crystallography. The authors have demostrated that compounds 447 can be used as oxidants for various substrates. Compared to the analogous noncyclic iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (HTIB), compounds 447 were generally more reactive in these reactions. In contrast, catalytic reactions using iodoarenes 446 as organocatalysts did not proceed efficiently.

165Nachtsheim and co-workers prepared pseudocyclic iodonium compound 449 by oxidation of iodobenzene 448 with 1H-pyrazole ring substituents at both ortho-positions (Scheme 157). The authors have also synthesized pseudocyclic compounds from iodoarenes with ortho-substituents other than pyrazole N-heterocycles, such as triazoles, benzimidazoles, and benzoxazoles. Compound 449 was found to perform as a useful oxidant for a variety of substrates. Interestingly, structure 449 resembles a pincer complex typical of transition metal complexes.

166Suero and co-workers found that reactions of alkynes 450 with pseudocyclic iodine reagents 451 acting as a carbyne source in the presence of rhodium catalyst produce cyclopropenium salts 452 (Scheme 158). This reaction can be performd only by using pseudocyclic iodine reagents; the analogous reactions with cyclic or noncyclic iodine(III) reagents do not give products 452. The authors suggest that this reaction mechanism involves initial formation of rhodium-carbynoid species, which reacts with an alkyne to yield final products. The resulting cyclopropenium salts 452 can be further reacted with appropriate nucleophiles to obtain the corresponding cyclopropenes as a single regioisomer.

167Pseudocyclic diaryliodonium compounds with a boronic acid group at the ortho-position of the iodine atom are unique reagents for generating aryne species under aqueous conditions, which can further react with various substrates to yield the corresponding products., Very recently, it was reported that the reaction of a pseudocyclic diaryliodonium compound 453 with sulfur compounds 454 under aqueous conditions at room temperature yields the corresponding sulfonium salts 455 in high yield (Scheme 159). Using sulfoxides instead of sulfides as substrates in this reaction leads to ortho-hydroxysulfonium compounds.

Catalytic Cycles Based on Iodine(III) Species

168Catalytic application of hypervalent iodine species is a hot topic in modern synthetic organic chemistry. An excellent book “Iodine Catalysis in Organic Synthesis” edited by Ishihara and Muñiz was published in 2022. Several recent reviews on this topic were also published.,,,, This section will provide an update on important development in this area published after 2021. Various catalytic reactions employing hypervalent iodine species generated from catalytic amounts of iodoarenes and stoichiometric oxidants have been reported since 2005., Numerous new iodoarenes were designed and utilized as organocatalysts under different reaction conditions. It should be noted that most of these reactions require a relatively large amount of iodoarene, up to 20–30%, which makes them different from the truly catalytic reactions of transition metals. mCPBA, Selectfluor, and Oxone are most commonly used as terminal oxidants to generate hypervalent iodine species from iodoarenes in these reactions. In recent years, reactions using oxygen as the terminal oxidant,, and electrochemical reactions have also been developed.− Gilmor and co-workers have reported the reaction of different iodoarenes with Selectfluor as the oxidant to generate the corresponding aryliodofluoronium species utilized in various catalytic fluorination reactions.− For example, enynes 456 react with Selectfluor (F-TEDA-BF4), and amine·HF in the presence of catalytic amounts of 4-iodotoluene to yield products of difluorination of the double bond (Scheme 160). The resulting products 457 can be further converted to a variety of compounds by appropriate treatment. The authors propose that the initially generated hypervalent iodine(III) species in this system react with the double bond followed by alkynyl group rearrangement to give final products 457. The same group also reported a difluorination reaction that utilizes an alkyl group shift instead of an alkynyl shift.

169Saito’s group reported the cycloisomerization-arylation of propargylic amides using F-TEDA-PF6, an analogue of Selectfluor, as a terminal oxidant with catalytic amounts of iodoarene in the presence of arenes. The reaction of propargylamides 458 with electron-rich arenes 459 and the oxidant F-TEDA-PF6 in the presence of catalytic iodoarene and DMSO affords oxazole compounds 460 (Scheme 161). The authors suggest a role for DMSO in the generation of sulfinyl fluoride active species (MeSOF) from DMSO and F-TEDA-PF6 and confirmed the presence of these species by 1H NMR. The same group has also reported the reaction using Bn2SO instead of DMSO and confirmed the presence of BnSOF active species by NMR. More recently, the authors have succeeded in developing a catalytic system combining TFDA-PF6 with Bn2SO and NsCl, which was utilized in the synthesis of furans from 2-propargyl-1,3-dicarbonyl compounds.

170König and co-workers reported catalytic reactions utilizing the generation of the corresponding (diacyloxyiodo)arenes from iodoarenes and carboxylic acids and Selectfluor., For example, carboxylic acids 461 under light irradiation in the presence of catalytic amounts of iodobenzene and stoichiometric Selectfluor in the presence of water and BF3 experience a Ritter-type reaction involving decarboxylation and resulting in the corresponding amides 462 (Scheme 162). Benzyl carboxylic acids and aliphatic carboxylic acids with primary, secondary, or tertiary carbon atoms can be used as substrates in this reaction. The authors assume that (diacyloxyiodo)arene is initially generated in the reaction system, which is then photolyzed to cleave the acyloxy groups and undergo decarboxylation to generate radical species, followed by conversion to cationic species, and finally trapping by nitrile to form final amide. The same authors have also reported a Ritter-type amination of benzylic compounds using radical species generated from (diacyloxyiodo)arene under similar reaction conditions.

171mCPBA and iodoarenes are a classic and the most common combination for generation of hypervalent iodine species in the reaction system., For example, when a catalytic amount of iodoarene and mCPBA as a terminal oxidant are added to phenylpropanamides 463, an intramolecular cyclization reaction proceeds, resulting in oxyindole compounds 464 (Scheme 163). This reaction in the presence of a chiral iodoarene yields the corresponding products with moderate enantioselectivity. The intramolecular cyclization in this reaction proceeds preferentially at the C–N bond rather than the C–O bond. On the other hand, when a substituent is introduced into the aromatic ring of the phenylpropanamide substrate, a competitive reaction involving the C–O and C–N bonds occurs, yielding two products.

172Jiang and co-workers reported enantioselective cycloamino fluorination of cinnamylbenzamide using BF3 as a fluorine source. The reaction using cinnamylbenzamides 465, chiral iodoarene, mCPBA, and BF3 yields the 6-membered ring products 466, while with the use of benzamides 467, the corresponding seven-membered ring products 468 are obtained (Scheme 164). The authors demonstrated that the reaction is substrate-specific, as the desired product is not produced when the length of the alkyl group is extended or when the aromatic ring is removed from the substrate. In the reactions using Py–HF or Et3N–HF instead of BF3, and in the reactions using PhIF2, no desired product was obtained, which suggests that BF3 is not only a fluorine source but is also an activator of the hypervalent iodine species produced in the reaction system. The authors have also investigated mechanisms of these reactions using computational methods.

173Zhang and co-workers have demonstrated that the reaction of various aryl carbonyl compounds 469 with chiral iodoarenes in the presence of mCPBA and TsOH proceeds as enantioselective tosyloxylation, yielding the corresponding α-tosyloxy compounds 470 (Scheme 165). The iodoarene used in this reaction is designed to introduce two sterically demanding BINOL functional groups around the iodine, thereby immobilizing the reaction field and preventing free rotation of the substituent. This catalytic design can also be used for intramolecular cyclization reactions. When 5-oxo-5-arylpentanoic acids are used as a substrate in the presence of TFA, the reaction proceeds enantioselectively as a lactonization reaction to afford the corresponding lactones. Wirth group has also reported the synthesis of chiral iodotriptycenes and their use for catalytic enantioselective α-tosyloxylation of propiophenone.

174As an example of a recent catalytic reaction using Oxone as an oxidant, Saito and co-workers reported the α-amidation of diketone compounds with iminoiodane species. This reaction was performed by the addition of TfNH2 and Oxone to 1,3-dicarbonyl compounds 471 in the presence of iodoarene, giving α-amide products 472 in moderate yield (Scheme 166). This catalytic reaction does not proceed with 1,3-carbonyl compounds bearing sterically bulky substituents. The authors have also succeeded in generating PhINTf from PhIO and TfNH2 and using it to obtain the desired products.

175De Vos and co-workers reported on the diacetoxylation of alkenes using an electrocatalytic method without the use of organic oxidants. The reaction takes place under Pt anode and Ni cathode conditions, and the reaction of alkenes 473, catalytic amounts of iodobenzene with BF3, acetic acid, and acetic anhydride gives the corresponding diacetoxy compounds 474 (Scheme 167). This reaction proceeds even when a carbon rod anode is used instead of the platinum anode. These reaction conditions can also be used for acetoxylactonization. In the reaction of an alkene with a cyclopropyl ring as a substrate, the products of the ring opening were obtained. The authors suggested that a one-electron oxidation mechanism was involved in this reaction.

Conclusion

176The literature summarized in this review reflects an increasing current interest in synthetic applications of hypervalent iodine(III) reagents. Just in 8 years after publication of our 2016 review, numerous new synthetic methodologies based on hypervalent iodine chemistry have been developed and increasingly employed in organic chemistry. Hypervalent iodine reagents are commercially available and environmentally safe compounds with diverse synthetic applications.

177Thousands of new research papers dedicated to various uses of hypervalent iodine compounds are published every year. Most of these papers deal with the classic, commercially available reagents, such as (diacetoxyiodo)benzene, (dichloroiodo)benzene, iodosylbenzene, 1-hydroxybenziodoxole, and various iodonium salts. At the same time, the newly deleloped cyclic reagents, including azido-, alkynyl-, and alkenylbenziodoxoles, are attracting significant research activity as the efficient group transfer reagents. Numerous new synthetic methodologies based on hypervalent iodine reagents have been developed recently. Most notably, catalytic and photocatalytic reactions of these compounds are gaining significant interest. Synthetic utilization of new hypervalent iodine reagents and catalytic systems, and the discovery of enantioselective reactions based on chiral hypervalent iodine reagents and catalysts has become an important direction in the field of modern hypervalent iodine chemistry.

178Hypervalent iodine reagents and synthetic methodologies involving hypervalent iodine species represent an essential tool of modern organic synthesis. Many synthetic applications of hypervalent iodine compounds are unique and cannot be achieved by using any alternative methods. We anticipate that the development of new reagents and synthetic methodologies based on hypervalent iodine chemistry will continue to be an active area of research in the future.

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49.
Robidas R.; Legault C. Y. Cyclic Haloiodanes: Syntheses, Applications and Fundamental Studies. Helv. Chim. Acta 2021, 104, e2100111.
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Yusubov M. S.; Zhdankin V. V. Zefirov’s Reagent and Related Hypervalent Iodine Triflates. Mendeleev Commun. 2021, 31, 282–287..
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Dasgupta A.; Thiehoff C.; Newman P. D.; Wirth T.; Melen R. L. Reactions Promoted by Hypervalent Iodine Reagents and Boron Lewis Acids. Org. Biomol. Chem. 2021, 19, 4852–4865..
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Chen C.; Wang X.; Yang T. Recent Synthetic Applications of the Hypervalent Iodine(III) Reagents in Visible-Light-Induced Photoredox Catalysis. Front. Chem. 2020, 8, 551159.
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Takenaga N.; Kumar R.; Dohi T. Heteroaryliodonium(III) Salts as Highly Reactive Electrophiles. Front. Chem. 2020, 8, 599026.
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Yang Y. O.; Wang X.; Xiao J.; Li Y.; Sun F.; Du Y. Formation of Carbon-Nitrogen Bond Mediated by Hypervalent Iodine Reagents Under Metal-free Conditions. Curr. Org. Chem. 2021, 25, 68–132..
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56.
Xiao X.; Wengryniuk S. E. Recent Advances in the Selective Oxidative Dearomatization of Phenols to o -Quinones and o -Quinols with Hypervalent Iodine Reagents. Synlett 2021, 32, 752–762..
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Kupwade R. V. A Concise Review of Hypervalent Iodine with Special Reference to Dess- Martin Periodinane. Mini-Rev. Org. Chem. 2020, 17, 946–957..
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58.
Wang Z. Innovation of Hypervalent(III) iodine in the Synthesis of Natural Products. New J. Chem. 2021, 45, 509–516..
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Shetgaonkar S. E.; Singh F. V. Hypervalent Iodine Reagents in Palladium-Catalyzed Oxidative Cross-Coupling Reactions. Front. Chem. 2020, 8, 705.
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Kumar R.; Sharma N.; Prakash O. Hypervalent Iodine Reagents in the Synthesis of Flavonoids and Related Compounds. Curr. Org. Chem. 2020, 24, 2031–2047..
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Saito A. Hypervalent Iodine-mediated/Catalyzed Oxidative Cycloisomerization/Annulation of Alkynes for Metal-free Synthesis of Oxazoles. Curr. Org. Chem. 2020, 24, 2048–2069..
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63.
Zheng H.; Xue X.-S. Recent Computational Studies on Mechanisms of Hypervalent Iodine(III)-Promoted Dearomatization of Phenols. Curr. Org. Chem. 2020, 24, 2106–2117..
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64.
Ghosh M. K.; Rout N. Aryl-Aryl Cross-Coupling with Hypervalent Iodine Reagents: Aryl Group Transfer Reactions. ChemistrySelect 2020, 5, 13644–13655..
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Wang Y.; Yang B.; Wu X.-X.; Wu Z.-G. Recent Application of Chiral Aryliodine Based on the 2-Iodoresorcinol Core in Asymmetric Catalysis. Synthesis 2021, 53, 889–903..
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The C3-H Bond Functionalization of Quinoxalin-2(1H)-Ones With Hypervalent Iodine(III) Reagents · 2020
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67.
Zhang B.; Li X.; Guo B.; Du Y. Hypervalent Iodine Reagent-Mediated Reactions Involving Rearrangement Processes. Chem. Commun. 2020, 56, 14119–14136..
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Budhwan R.; Garg G.; Namboothiri I. N. N.; Murarka S. Hypervalent Iodine(III) Reagents in the Synthesis of Heterocyclic Compounds. Targets Heterocycl. Syst. 2019, 23, 27–52..
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Han Z.-Z.; Zhang C.-P. Fluorination and Fluoroalkylation Reactions Mediated by Hypervalent Iodine Reagents. Adv. Synth. Catal. 2020, 362, 4256–4292..
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Vlasenko Y. A.; Yusubov M. S.; Shafir A.; Postnikov P. S. Hypervalent Iodine in the Structure of N-Heterocycles: Synthesis, Structure, and Application in Organic Synthesis. Chem. Heterocycl. Compd. 2020, 56, 854–866..
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Zhao R.; Shi L. Reactions between Diazo Compounds and Hypervalent Iodine(III) Reagents. Angew. Chem., Int. Ed. 2020, 59, 12282–12292..
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Han J.; Butler G.; Moriwaki H.; Konno H.; Soloshonok V. A.; Kitamura T. Kitamura Electrophilic Fluorination using HF as a Source of Fluorine. Molecules 2020, 25, 2116.
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Yoshimura A.; Saito A.; Yusubov M. S.; Zhdankin V. V. Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions. Synthesis 2020, 52, 2299–2310..
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Li X.; Liu T.; Zhang B.; Zhang D.; Shi H.; Yu Z.; Tao S.; Du Y. Formation of Carbon-Carbon Bonds Mediated by Hypervalent Iodine Reagents Under Metal-free Conditions. Curr. Org. Chem. 2020, 24, 74–103..
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75.
Kiyokawa K.; Minakata S. Iodine-Based Reagents in Oxidative Amination and Oxygenation. Synlett 2020, 31, 845–855..
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Banerjee S.; Bhoyare V. W.; Patil N. T. Gold and Hypervalent Iodine(III): liaisons Over a Decade for Electrophilic Functional Group Transfer Reactions. Chem. Commun. 2020, 56, 2677–2690..
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Yusubov M. S.; Postnikov P.; Yoshimura A.; Zhdankin V. V. Benziodoxole-Derived Organosulfonates: The Strongest Hypervalent Iodine Electrophiles and Oxidants. Synlett 2020, 31, 315–326..
Not in our library10.1055/s-0039-1690761
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Reddy Kandimalla S.; Prathima Parvathaneni S.; Sabitha G.; Subba Reddy B. V. Recent Advances in Intramolecular Metal-Free Oxidative C-H Bond Aminations Using Hypervalent Iodine(III) Reagents. Eur. J. Org. Chem. 2019, 2019, 1687–1714..
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Muniz K. Promoting Intermolecular C-N Bond Formation under the Auspices of Iodine(III). Acc. Chem. Res. 2018, 51, 1507–1519..
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Arnold A. M.; Ulmer A.; Gulder T. Advances in Iodine(III)-Mediated Halogenations: A Versatile Tool to Explore New Reactivities and Selectivities. Chem. - Eur. J. 2016, 22, 8728–8739..
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Kohlhepp S. V.; Gulder T. Hypervalent Iodine(III) Fluorinations of Alkenes and Diazo Compounds: New Opportunities in Fluorination Chemistry. Chem. Soc. Rev. 2016, 45, 6270–6288..
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Budhwan R.; Yadav S.; Murarka S. Late Stage Functionalization of Heterocycles Using Hypervalent Iodine(III) Reagents. Org. Biomol. Chem. 2019, 17, 6326–6341..
Not in our library10.1039/c9ob00694j
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Fujita M. Enantioselective Heterocycle Formation Using Chiral Hypervalent Iodine(III). Heterocycles 2018, 96, 563–594..
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Murarka S.; Antonchick A. P. Oxidative Heterocycle Formation Using Hypervalent Iodine(III) Reagents. Top. Curr. Chem. 2015, 373, 75–104..
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Yoshimura A.; Zhdankin V. V. Oxidative Cyclizations of Oximes Using Hypervalent Iodine Reagents. ARKIVOC 2017, 2017 (i), 99–116..
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92.
Dohi T.; Kita Y. Hypervalent Iodine-Induced Oxidative Couplings (New Metal-Free Coupling Advances and their Applications in Natural Product Syntheses). Top. Curr. Chem. 2016, 373, 1–24..
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Flores A.; Cots E.; Berges J.; Muniz K. Enantioselective Iodine(I/III) Catalysis in Organic Synthesis. Adv. Synth. Catal. 2019, 361, 2–25..
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Ghosh S.; Pradhan S.; Chatterjee I. A Survey of Chiral Hypervalent Iodine Reagents in Asymmetric Synthesis. Beilstein J. Org. Chem. 2018, 14, 1244–1262..
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Kumar R.; Wirth T. Asymmetric Synthesis with Hypervalent Iodine Reagents. Top. Curr. Chem. 2015, 373, 243–262..
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96.
Aradi K.; Toth B. L.; Tolnai G. L.; Novak Z. Diaryliodonium Salts in Organic Syntheses: A Useful Compound Class for Novel Arylation Strategies. Synlett 2016, 27, 1456–1485..
Not in our library10.1055/s-0035-1561369
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Kumar D.; Arun V.; Pilania M.; Mehra M. K.; Khandagale S. B. Diaryliodonium Salts: Emerging Reagents for Arylations and Heterocycles Synthesis. Chem. Biol. Interface 2016, 6, 270–281.
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98.
Wang M.; Chen S.; Jiang X. Atom-Economical Applications of Diaryliodonium Salts. Chem. - Asian J. 2018, 13, 2195–2207..
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Olofsson B. Arylation with Diaryliodonium Salts. Top. Curr. Chem. 2015, 373, 135–166..
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Yoshimura A.; Saito A.; Zhdankin V. V. Iodonium Salts as Benzyne Precursors. Chem. - Eur. J. 2018, 24, 15156–15166..
Not in our library10.1002/chem.201802111
101.
Chatterjee N.; Goswami A. Synthesis and Application of Cyclic Diaryliodonium Salts: A Platform for Bifunctionalization in a Single Step. Eur. J. Org. Chem. 2017, 2017, 3023–3032..
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Preshlock S.; Tredwell M.; Gouverneur V. 18F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography. Chem. Rev. 2016, 116, 719–766..
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Bernard-Gauthier V.; Lepage M. L.; Waengler B.; Bailey J. J.; Liang S. H.; Perrin D. M.; Vasdev N.; Schirrmacher R. Recent advances in 18F radiochemistry: a Focus on B-18F, Si-18F, Al-18F, and C-18F Radiofluorination via Spirocyclic Iodonium Ylides. J. Nucl. Med. 2018, 59, 568–572..
Not in our library10.2967/jnumed.117.197095
104.
Yusubov M. S.; Yoshimura A.; Zhdankin V. V. Iodonium Ylides in Organic Synthesis. ARKIVOC 2017, 2016 (i), 342–374..
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105.
Boelke A.; Finkbeiner P.; Nachtsheim B. J. Atom-Economical Group-Transfer Reactions with Hypervalent Iodine Compounds. Beilstein J. Org. Chem. 2018, 14, 1263–1280..
Not in our library10.3762/bjoc.14.108
106.
Hari D. P.; Caramenti P.; Waser J. Cyclic Hypervalent Iodine Reagents: Enabling Tools for Bond Disconnection via Reactivity Umpolung. Acc. Chem. Res. 2018, 51, 3212–3225..
Not in our library10.1021/acs.accounts.8b00468
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Li Y.; Hari D. P.; Vita M. V.; Waser J. Cyclic Hypervalent Iodine Reagents for Atom-Transfer Reactions: Beyond Trifluoromethylation. Angew. Chem., Int. Ed. 2016, 55, 4436–4454..
Not in our library10.1002/anie.201509073
108.
Fruh N.; Charpentier J.; Togni A. Iodanes as Trifluoromethylation Reagents. Top. Curr. Chem. 2015, 373, 167–186..
Not in our library10.1007/128_2015_658
109.
Waser J. Benziodoxol(on)e Reagents as Tools in Organic Synthesis: The Background behind the Discovery at the Laboratory of Catalysis and Organic Synthesis. Synlett 2016, 27, 2761–2773..
Not in our library10.1055/s-0036-1589409
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Waser J. Alkynylation with Hypervalent Iodine Reagents. Top. Curr. Chem. 2015, 373, 187–222..
Not in our library10.1007/128_2015_660
111.
Olding A.; Ho C. C. Recent Applications of the Zhdankin Reagent in Organic Synthesis. Aust. J. Chem. 2019, 72, 646–648..
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Wang X.; Studer A. Iodine(III) Reagents in Radical Chemistry. Acc. Chem. Res. 2017, 50, 1712–1724..
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Wang L.; Liu J. Synthetic Applications of Hypervalent Iodine(III) Reagents Enabled by Visible Light Photoredox Catalysis. Eur. J. Org. Chem. 2016, 2016, 1813–1824..
Not in our library10.1002/ejoc.201501490
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Yoshimura A.; Yusubov M. S.; Zhdankin V. V. Synthetic Applications of Pseudocyclic Hypervalent Iodine Compounds. Org. Biomol. Chem. 2016, 14, 4771–4781..
Not in our library10.1039/c6ob00773b
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Han Y.-C.; Zhang C. Synthetic Application of Water-Soluble Hypervalent Iodine Reagents in Aqueous Media. Tetrahedron Lett. 2018, 59, 3052–3064..
Not in our library10.1016/j.tetlet.2018.06.059
116.
Gayen K. S.; Chatterjee N.; Khamarui S.; Tarafdar P. K. Recent Advances in Iodosobenzene-Mediated Construction of Heterocyclic Scaffolds: Transition-Metal-Free Approaches and Scope. Eur. J. Org. Chem. 2018, 2018, 425–439..
Not in our library10.1002/ejoc.201701306
117.
Lee J. H.; Choi S.; Hong K. B. Alkene Difunctionalization Using Hypervalent Iodine Reagents: Progress and Developments in the Past Ten Years. Molecules 2019, 24, 2634.
Not in our library10.3390/molecules24142634
118.
Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes · 2018
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119.
Xing L.; Zhang Y.; Du Y. Hypervalent Iodine-Mediated Synthesis of Spiroheterocycles via Oxidative Cyclization. Curr. Org. Chem. 2019, 23, 14–37..
Not in our library10.2174/1385272822666181211122802
120.
Ghosh M. K.; Rajkiewicz A. A.; Kalek M. Organocatalytic Group Transfer Reactions with Hypervalent Iodine Reagents. Synthesis 2019, 51, 359–370..
Not in our library10.1055/s-0037-1609639
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Singh F. V.; Kole P. B.; Mangaonkar S. R.; Shetgaonkar S. E. Synthesis of Spirocyclic Scaffolds Using Hypervalent Iodine Reagents. Beilstein J. Org. Chem. 2018, 14, 1778–1805..
Not in our library10.3762/bjoc.14.152
122.
Quideau S.; Pouysegu L.; Peixoto P. A.; Deffieux D. Phenol Dearomatization with Hypervalent Iodine Reagents. Top. Curr. Chem. 2016, 373, 25–74..
Not in our library10.1007/128_2015_665
123.
Maertens G.; Canesi S. Rearrangements Induced by Hypervalent Iodine. Top. Curr. Chem. 2015, 373, 223–241..
Not in our library10.1007/128_2015_657
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Murphy G. K.; Racicot L.; Carle M. S. The Chemistry between Hypervalent Iodine(III) Reagents and Organophosphorus Compounds. Asian J. Org. Chem. 2018, 7, 837–851..
Not in our library10.1002/ajoc.201800058
125.
Sousa e Silva F.; Tierno A.; Wengryniuk S. Hypervalent Iodine Reagents in High Valent Transition Metal Chemistry. Molecules 2017, 22, 780.
Not in our library10.3390/molecules22050780
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Elsherbini M.; Wirth T. Hypervalent Iodine Reagents by Anodic Oxidation: A Powerful Green Synthesis. Chem. - Eur. J. 2018, 24, 13399–13407..
Not in our library10.1002/chem.201801232
127.
Maity A.; Powers D. C. Hypervalent Iodine Chemistry as a Platform for Aerobic Oxidation Catalysis. Synlett 2019, 30, 257–262..
Not in our library10.1055/s-0037-1610338
128.
Asandei A. D. Photomediated Controlled Radical Polymerization and Block Copolymerization of Vinylidene Fluoride. Chem. Rev. 2016, 116, 2244–2274..
Not in our library10.1021/acs.chemrev.5b00539
129.
Yusubov M. S.; Yoshimura A.; Zhdankin V. V. Hypervalent Iodine Compounds as Polymerization Initiators. New Mater., Compd. Appl. 2019, 3, 5–14.
Not in our library
130.
Le Du E.; Waser J. Recent Progress in Alkynylation with Hypervalent Iodine Reagents. Chem. Commun. 2023, 59, 1589–1604..
Not in our library10.1039/d2cc06168f
131.
Upadhyaya K.; Dubbu S. Advancing Carbohydrate Functionality: the Role Of Hypervalent Iodine. Carbohydr. Res. 2024, 542, 109175.
Not in our library10.1016/j.carres.2024.109175
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Bauer A.; Maulide N. Recent Discoveries on the Structure of Iodine(III) Reagents and their Use in Cross-Nucleophile Coupling. Chem. Sci. 2021, 12, 853–864..
Not in our library10.1039/d0sc03266b
133.
Shetgaonkar S. E.; Raju A.; China H.; Takenaga N.; Dohi T.; Singh F. V. Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents. Front. Chem. 2022, 10, 909250.
Not in our library10.3389/fchem.2022.909250
134.
Hui C.; Antonchick A. P. Iodonitrene: a Direct Metal-Free Electrophilic Aminating Reagent. Org. Chem. Front. 2022, 9, 3897–3907..
Not in our library10.1039/d2qo00739h
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Jalil A.; Yang Y. O.; Chen Z.; Jia R.; Bi T.; Li X.; Du Y. Formation of Carbon-Oxygen Bond Mediated by Hypervalent Iodine Reagents Under Metal-Free Conditions. Mini-Rev. Org. Chem. 2021, 18, 540–605..
Not in our library10.2174/1570193x17999200807140943
136.
Cheng Y.; Li G.; Jiang L.; Dong Y.; Zhan X.; Sun F.; Du Y. Construction of C-S and C-Se Bonds Mediated by Hypervalent Iodine Reagents Under Metal-Free Conditions. Curr. Org. Chem. 2022, 26, 1935–1953..
Not in our library10.2174/1385272826666220620153347
137.
Zhao Y.; Duan Y.; Shi S.; Bai Y.; Huang L.; Yang X.; Zhang Y.; Feng B.; Zhang J.; Zhang Q. Recent Advances of Hypervalent Iodine (III) Reagents upon Visible Light Irradiation. Chin. J. Org. Chem. 2023, 43, 4106–4140..
Not in our library10.6023/cjoc202305022
138.
Claraz A.; Masson G. Asymmetric Iodine Catalysis-Mediated Enantioselective Oxidative Transformations. Org. Biomol. Chem. 2018, 16, 5386–5402..
Not in our library10.1039/c8ob01378k
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Sakthivel K.; Kole P. B.; Mamgain R.; Singh F. V. Iodine(III)-Based Hypervalent Iodine Electrophiles in Organic Synthesis. Curr. Org. Chem. 2022, 26, 1917–1934..
Not in our library10.2174/1385272827666230103110651
140.
Segura-Quezada L. A.; Torres-Carbajal K. R.; Juarez-Ornelas K. A.; Navarro-Santos P.; Granados-Lopez A. J.; Gonzalez-Garcia G.; Ortiz-Alvarado R.; de Leon-Solis C.; Solorio-Alvarado C. R. Iodine(III)-Mediate Oxidative Cyanation, Azidation, Nitration, Sulfenylation and Selenization in Olefins and Aromatic Systems. Curr. Org. Chem. 2022, 26, 1954–1968..
Not in our library10.2174/1385272826666220621142211
141.
Chen W. W.; Cuenca A. B.; Shafir A. The Power of Iodane-Guided C-H Coupling: A Group-Transfer Strategy in Which a Halogen Works for Its Money. Angew. Chem., Int. Ed. 2020, 59, 16294–16309..
Not in our library10.1002/anie.201908418
142.
Sakthivel K.; J S.; Raju A.; Kumar R.; Dohi T.; Singh F. V. Recent Progress in Hypervalent Iodine-Mediated Fluorination of Organic Compounds. ARKIVOC 2023, 2022 (vii), 138–165..
Not in our library10.24820/ark.5550190.p011.996
143.
Kretzschmar M.; Gulder T. Discovering the Site-Selective Umpolung of Ketones Triggered by Hypervalent Fluoro-Iodanes - Why Investigating Side Reactions Matters!. Synlett 2023, 34, 405–413..
Not in our library10.1055/a-1990-5495
144.
Li Q.; Liu X.-B.; Wang H. Iodine(III)-Mediated Migratory gem-Difluorinations: Synthesis of β Transformable Functionality Substituted gem-Difluoroalkanes. Chem. Rec. 2023, 23, e202300231.
Not in our library10.1002/tcr.202300231
145.
Segura-Quezada L. A.; Torres-Carbajal K. R.; Satkar Y.; Juarez Ornelas K. A.; Mali N.; Patil D. B.; Gamez-Montano R.; Zapata-Morales J. R.; Lagunas-Rivera S.; Ortiz-Alvarado R.; Solorio-Alvarado C. R. Oxidative Halogenation of Arenes, Olefins and Alkynes Mediated by Iodine(III) Reagents. Mini-Rev. Org. Chem. 2021, 18, 159–172..
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146.
Zhang H.; Xu N.; Tang R.; Shi X. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents. Chin. J. Org. Chem. 2023, 43, 3784–3805..
Not in our library10.6023/cjoc202304008
147.
Alam M. M.; Bollikolla H. B.; Amanullah M.; Hussein M.; Varala R. Phenyliodine(III)diacetate (PIDA): Applications in Rearrangement/Migration Reactions. Curr. Org. Chem. 2023, 27, 93–107..
Not in our library10.2174/1385272827666230330105241
148.
Shetgaonkar S. E.; Krishnan M.; Singh F. V. Hypervalent Iodine Reagents for Oxidative Rearrangements. Mini-Rev. Org. Chem. 2021, 18, 138–158..
Not in our library10.2174/1570193x17999200727204349
149.
Chatterjee N.; Goswami A. Diverse Transformations of Boronic Compounds Promoted by Hypervalent Organoiodines(III): Unique Combined Reactivity of Two Electrophilic Compounds. Adv. Synth. Catal. 2017, 359, 358–371..
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Zhang X.; Cong Y.; Lin G.; Guo X.; Cao Y.; Lei K.; Du Y. Recent Advances of the Application of Organoiodine(III) Reagents in the Construction of Heterocyclic Compounds. Chin. J. Org. Chem. 2016, 36, 2513–2529..
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Poynder T. B.; Chamorro Orue A. I.; Tania; Sharp-Bucknall L.; Flynn M. T.; Wilson D. J. D.; Athukorala Arachchige K. S.; Clegg J. K.; Dutton J. L. On the Activation of PhICl2 with Pyridine. Chem. Commun. 2021, 57, 4970–4973..
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Koichi S.; Leuthold B.; Luthi H. P. Why do the Togni Reagent and Some ff its Derivatives Exist in the High-Energy Hypervalent Iodine Form? New Insight into the Origins of Their Kinetic Stability. Phys. Chem. Chem. Phys. 2017, 19, 32179–32183..
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Shao Y.; Ren Z.; Zheng C.; Xue X.-S. Computational Insights into the Reactivity Difference between Hypervalent Bromine(III) and Hypervalent Iodine(III) Reagent in the C–H Amination and Alkene Aziridination. Adv. Synth. Catal. 2023, 365, 2737–2743..
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Yang J.-D.; Li M.; Xue X.-S. Computational I(III)-X BDEs for Benziodoxol(on)e-based Hypervalent Iodine Reagents: Implications for Their Functional Group Transfer Abilities. Chin. J. Chem. 2019, 37, 359–363..
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Sreenithya A.; Patel C.; Hadad C. M.; Sunoj R. B. Hypercoordinate Iodine Catalysts in Enantioselective Transformation: The Role of Catalyst Folding in Stereoselectivity. ACS Catal. 2017, 7, 4189–4196..
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Lv W.-X.; Li Q.; Li J.-L.; Li Z.; Lin E.; Tan D.-H.; Cai Y.-H.; Fan W.-X.; Wang H. gem-Difluorination of Alkenyl N-methyliminodiacetyl Boronates: Synthesis of α- and β-Difluorinated Alkylborons. Angew. Chem., Int. Ed. 2018, 57, 16544–16548..
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Yang S.; Liu X.-B.; Feng S.-X.; Li Y.; Tu F.-H.; Huang B.; Huang L.-L.; Huang Z.-S.; Wang H.; Li Q. Hypervalent Iodine(III)-Mediated Ring-Expansive Difluorination of Alkynylcyclopropanes En Route to the Synthesis of Difluorinated Alkylidenecyclobutanes. Org. Chem. Front. 2022, 9, 4447–4452..
Not in our library10.1039/d2qo00888b
247.
Noorollah J.; Im H.; Siddiqi F.; Singh N.; Spatola N. R.; Chaudhry A.; Jones T. J.; Hyatt I. F. D. para-Selective Benzylation of Aryl Iodides by the in situ Preparation of ArIF2: a Hypervalent Iodine-Guided Electrophilic Substitution. Eur. J. Org. Chem. 2020, 2020, 2302–2305..
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Haupt J. D.; Berger M.; Waldvogel S. R. Electrochemical Fluorocyclization of N-Allylcarboxamides to 2-Oxazolines by Hypervalent Iodine Mediator. Org. Lett. 2019, 21, 242–245..
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Panda C.; Doyle L. M.; Gericke R.; McDonald A. R. Rapid Iron(III)-Fluoride-Mediated Hydrogen Atom Transfer. Angew. Chem., Int. Ed. 2021, 60, 26281–26286..
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Panda C.; Anny-Nzekwue O.; Doyle L. M.; Gericke R.; McDonald A. R. Evidence for a High-Valent Iron-Fluoride that Mediates Oxidative C(sp3)-H Fluorination. JACS Au 2023, 3, 919–928..
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Qi X.; Yu F.; Chen P.; Liu G. Intermolecular Palladium-Catalyzed Oxidative Fluorocarbonylation of Unactivated Alkenes: Efficient Access to β-Fluorocarboxylic Esters. Angew. Chem., Int. Ed. 2017, 56, 12692–12696..
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Cao Y.; Sayala K. D.; Gamage P. L.; Kumar R.; Tsarevsky N. V. Synthesis of Fluorine-Containing Polymers by Functionalization of cis-1,4-Polyisoprene with Hypervalent Iodine Compounds. Macromolecules 2020, 53, 8020–8031..
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253.
Huang L.-L.; Lin P.-P.; Li Y.-X.; Feng S.-X.; Tu F.-H.; Yang S.; Zhao G.-Y.; Huang Z.-S.; Wang H.; Li Q. Oxidative Fluoroarylation of Benzylidenecyclopropanes with HF·Py and Aryl Iodides via Iodonio-[3,3]-Rearrangement. Org. Lett. 2022, 24, 3389–3394..
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254.
Li C.; Liao Y.; Tan X.; Liu X.; Liu P.; Lv W.-X.; Wang H. Hypervalent Iodine-Mediated gem-Difluorination of Vinyl Halides Enabled by Exclusive 1,2-Halo Migration. Sci. China: Chem. 2021, 64, 999–1003..
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255.
Sarie J. C.; Neufeld J.; Daniliuc C. G.; Gilmour R. Willgerodt-Type Dichloro(aryl)-λ3-Iodanes: A Structural Study. Synthesis 2019, 51, 4408–4416..
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256.
Mukherjee T.; Biswas S.; Ehnbom A.; Ghosh S. K.; El-Zoghbi I.; Bhuvanesh N.; Bazzi H. S.; Gladysz J. A. Syntheses, Structures, and Stabilities of Aliphatic And Aromatic Fluorous Iodine(I) and Iodine(III) Compounds: the Role of Iodine Lewis Basicity. Beilstein J. Org. Chem. 2017, 13, 2486–2501..
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Granados A.; Jia Z.; del Olmo M.; Vallribera A. In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes. Eur. J. Org. Chem. 2019, 2019, 2812–2818..
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Cheng X.; Yin Q.; Jiang Y.-X.; Jiang L.-F.; Li S.-Y.; Cheng Y.-F.; Sun X.-C.; Peng L.; Zhong C.; Deng Q.-H. Simple and Versatile Nitrooxylation: Noncyclic Hypervalent Iodine Nitrooxylating Reagent. Angew. Chem., Int. Ed. 2023, 62, e202302521.
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Zhou J.; Song X.-X.; Zhao C.-B.; Wang L.-L.; Zhang X.-Q.; Chen Y.; Zhang L. DFT Study on Oxidative Cyclization of o-Alkynylbenzoates Mediated by Hypervalent Iodine Reagent: Mechanism and Substituent Effect. ChemistrySelect 2020, 5, 3113–3118..
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260.
Canestrari D.; Lancianesi S.; Badiola E.; Strinna C.; Ibrahim H.; Adamo M. F. A. Desulfurative Chlorination of Alkyl Phenyl Sulfides. Org. Lett. 2017, 19, 918–921..
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261.
Tao J.; Tuck T. N.; Murphy G. K. Geminal Dichlorination of Phenyliodonium Ylides of β-Dicarbonyl Compounds through Double Ligand Transfer from (Dichloroiodo)benzene. Synthesis 2016, 48, 772–782..
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262.
Carle M. S.; Shimokura G. K.; Murphy G. K. Iodobenzene Dichloride in the Esterification and Amidation of Carboxylic Acids: In-Situ Synthesis of Ph3PCl2. Eur. J. Org. Chem. 2016, 2016, 3930–3933..
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263.
Wang Y.-M.; He P.; Peng X.; Liu S.-Q.; Yi X.-Y. Chlorogenation of Pyrrole-Based on Di(Pyridyl)Pyrrolide Ligand and Synthesis of its Ruthenium Carbonyl Complexes. Polyhedron 2019, 168, 67–71..
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Xu D.; Sun W.-W.; Xie Y.; Liu J.-K.; Liu B.; Zhou Y.; Wu B. Metal-Free Regioselective Hypervalent Iodine-Mediated C-2 and C-3 Difunctionalization of N-Substituted Indoles. J. Org. Chem. 2016, 81, 11081–11094..
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Gair J. J.; Haines B. E.; Filatov A. S.; Musaev D. G.; Lewis J. C. Mono-N-protected Amino Acid Ligands Stabilize Dimeric Palladium(II) Complexes of Importance to C-H Functionalization. Chem. Sci. 2017, 8, 5746–5756..
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266.
Fujimoto K.; Izawa S.; Arikai Y.; Sugimoto S.; Oue H.; Inuzuka T.; Uemura N.; Sakamoto M.; Hiramoto M.; Takahashi M. Regioselective Bay-Functionalization of Perylenes Toward Tailor-Made Synthesis of Acceptor Materials for Organic Photovoltaics. ChemPlusChem. 2020, 85, 285–293..
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267.
Cao J.; Ma Y.; Hu L.; Xia W.; Zhang X.; Xiong Y. Polyhalogenation-Facilitated Spirolactonization at the meta-Position of Phenols. J. Org. Chem. 2023, 88, 1075–1084..
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Yun Z.; Cheng R.; Sun J.; Zhang-Negrerie D.; Du Y. Iodobenzene Dichloride/Zinc Chloride-Mediated Synthesis of N-Alkoxyindole-3-carbonitriles from 3-Alkoxyimino-2-arylalkylnitriles via Intramolecular Heterocyclization. Adv. Synth. Catal. 2018, 360, 250–254..
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269.
Dai P.-F.; Xu H. Novel Chlorination of Imidazo-Fused Heterocycles via Dichloro(aryl)-λ3-iodanes. Eur. J. Org. Chem. 2022, 2022, e202200779.
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Davis B. A.; Tania; Dutton J. L. Kinetic Study on the Activation of PhICl2 with Lewis Bases for Aromatic Chlorination. Dalton Trans. 2022, 51, 12384–12388..
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271.
Tania; Poynder T. B.; Kaur A.; Barwise L.; Houston S. D.; Nair A. J.; Clegg J. K.; Wilson D. J. D.; Dutton J. L. PhICl2 is Activated by Chloride Ions. Dalton Trans. 2021, 50, 11986–11991..
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Poynder T. B.; Houston S. D.; Dutton J. L. [Ag]2[B12Cl12] as a Catalyst in PhICl2 Mediated Chlorination. Eur. J. Org. Chem. 2021, 2021, 2788–2791..
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Zhang H.; Shi D.; Ren S.; Jin H.; Liu Y. Selective gem-Dichlorination of Isonitriles Mediated by (Dichloroiodo)benzene. Eur. J. Org. Chem. 2016, 2016, 4224–4229..
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274.
Xing L.; Zhang Y.; Zhang Y.; Ai Z.; Li X.; Du Y.; Deng J.; Zhao K. Regioselective Chlorolactonization of Styrene-Type Carboxylic Esters and Amides via PhICl2-Mediated Oxidative C-O/C-Cl Bond Formations. J. Org. Chem. 2019, 84, 13832–13840..
Not in our library10.1021/acs.joc.9b02022
275.
Xing L.; Zhang Y.; Li B.; Du Y. Synthesis of 4-Chloroisocoumarins via Intramolecular Halolactonization of o-Alkynylbenzoates: PhICl2-Mediated C-O/C-Cl Bond Formation. Org. Lett. 2019, 21, 1989–1993..
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276.
Shang Z.; Chen Q.; Xing L.; Zhang Y.; Wait L.; Du Y. In situ Formation of RSCl/ArSeCl and Their Oxidative Coupling with Enaminone Derivatives Under Transition-metal Free Conditions. Adv. Synth. Catal. 2019, 361, 4926–4932..
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277.
Xing L.; Zhang Y.; Li B.; Du Y. In Situ Formation of RSCl/ArSeCl and Their Application to the Synthesis of 4-Chalcogenylisocumarins/Pyrones from o-(1-Alkynyl)benzoates and (Z)-2-Alken-4-ynoates. Org. Lett. 2019, 21, 3620–3624..
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278.
Li J.; Li B.; Chen J.; Jia X.; Wang M.; Hao C.; Zheng X.; Dai H.; Hu W. Catalyst-Free gem-Chlorosulfurization of Difluoromethyl-Substituted Diazo Compounds with Disulfide and PhICl2. Org. Biomol. Chem. 2021, 19, 8030–8034..
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279.
Yu Z.; Zhang D.; Li X.; Zhang B.; Yang Z.; Qian Y.; Du Y. Synthesis of 4-Chalcogenylated Isoxazoles Mediated by PhICl2 and Diorganyl Disulfides/Diselenides. Asian J. Org. Chem. 2021, 10, 3015–3019..
Not in our library10.1002/ajoc.202100599
280.
Zhang L.; Qi L.; Chen J.-M.; Dong W.; Fang Z.-Y.; Cao T.-Y.; Li W.; Wang L.-J. Preparation of Selenyl 1,3-Oxazines via PhICl2/Cu2O-Promoted Aminoselenation of O-Homoallyl Benzimidates with Diselenides. Chem. Commun. 2021, 57, 12655–12658..
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281.
Zhang B.; Li X.; Ai Z.; Zhao B.; Yu Z.; Du Y. Chemoselective Synthesis of Sulfenylated Spiroindolenines from Indolyl-ynones via Organosulfenyl Chloride-Mediated Dearomatizing Spirocyclization. Org. Lett. 2022, 24, 390–394..
Not in our library10.1021/acs.orglett.1c04063
282.
Yu M.; Jin T.; Wang X.; Li H.; Ji D.; Yao J.; Zeng H.; Shi S.; Xu K.; Zhang L. Regioselective Intramolecular Cyclization of o-Alkynyl Arylamines with the In Situ Formation of ArXCl to Construct Poly-Functionalized 3-Selenylindoles. RSC Adv. 2023, 13, 6210–6216..
Not in our library10.1039/d3ra00030c
283.
Zhang B.; Li X.; Li X.; Yu Z.; Zhao B.; Wang X.; Du Y.; Zhao K. An Interrupted Pummerer Reaction Mediated by a Hypervalent Iodine(III) Reagent: In Situ Formation of RSCl and Its Application for the Synthesis of 3-Sulfenylated Indoles. J. Org. Chem. 2021, 86, 17274–17281..
Not in our library10.1021/acs.joc.1c02404
284.
Tao S.; Xu L.; Yang K.; Zhang J.; Du Y. Construction of the 2-Amino-1,3-selenazole Skeleton via PhICl2/KSeCN-Mediated Selenocyanation/Cyclization. Org. Lett. 2022, 24, 4187–4191..
Not in our library10.1021/acs.orglett.2c01468
285.
Tao S.; Jiang L.; Du Y. Electrophilic Oxythio/selenocyanation of o-Alkenyl Benzoic Acids: Divergent Synthesis of Thio/selenocyanated Isobenzofuranones and Isocoumarins. Asian J. Org. Chem. 2022, 11, e202200595.
Not in our library10.1002/ajoc.202200595
286.
Tao S.; Huo A.; Gao Y.; Zhang X.; Yang J.; Du Y. PhICl2-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of O-(1-Alkynyl)Benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins. Front. Chem. 2022, 10, 859995.
Not in our library10.3389/fchem.2022.859995
287.
Liu L.; Gu Y.-C.; Zhang C.-P. Palladium-Catalyzed C-H Trifluoromethylselenolation of Arenes with [Me4N][SeCF3] and an Oxidant. Chem. Commun. 2022, 58, 9238–9241..
Not in our library10.1039/d2cc02897b
288.
Yin C.; Hu P. Visible-Light-Induced Cross-Dehydrogenative Coupling of Heteroarenes with Aliphatic Alcohols Mediated by Iodobenzene Dichloride. Eur. J. Org. Chem. 2023, 26, e202300015.
Not in our library10.1002/ejoc.202300015
289.
Gericke R.; Doyle L. M.; Farquhar E. R.; McDonald A. R. Oxo-Free Hydrocarbon Oxidation by an Iron(III)-Isoporphyrin Complex. Inorg. Chem. 2020, 59, 13952–13961..
Not in our library10.1021/acs.inorgchem.0c01618
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Johnson E. J.; Kleinlein C.; Musgrave R. A.; Betley T. A. Diiron Oxo Reactivity in a Weak-Field Environment. Chem. Sci. 2019, 10, 6304–6310..
Not in our library10.1039/c9sc00605b
291.
Na H.; Watson M. B.; Tang F.; Rath N. P.; Mirica L. M. Photoreductive Chlorine Elimination from a Ni(III)Cl2 Complex Supported by a Tetradentate Pyridinophane Ligand. Chem. Commun. 2021, 57, 7264–7267..
Not in our library10.1039/d1cc02114a
292.
Sousa e Silva F. C.; Bloomer B. J.; Wengryniuk S. E. Reactivity of (NNN)-Pincer Nickel(II) Aryl Complex towards Oxidative Carbon-Heteroatom Bond Formation. Tetrahedron 2018, 74, 3278–3282..
Not in our library10.1016/j.tet.2018.04.029
293.
Diccianni J. B.; Hu C.; Diao T. Binuclear, High-Valent Nickel Complexes: Ni-Ni Bonds in Aryl-Halogen Bond Formation. Angew. Chem., Int. Ed. 2017, 56, 3635–3639..
Not in our library10.1002/anie.201611572
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Wang B.; Barnes J.; Ferrara S. J.; Sproules S.; Zhang X.; Mague J. T.; Donahue J. P. Fully Reduced and Mixed-Valent Multi-Copper Aggregates Supported by Tetradentate Diamino Bis(thiolate) Ligands. Inorg. Chem. 2023, 62, 9854–9871..
Not in our library10.1021/acs.inorgchem.3c00784
295.
Belli R. G.; Tafuri V. C.; Roberts C. C. Improving Alkyl-Alkyl Cross-Coupling Catalysis with Early Transition Metals through Mechanistic Understanding and Metal Tuning. ACS Catal. 2022, 12, 9430–9436..
Not in our library10.1021/acscatal.2c02785
296.
Ng W.-M.; Guo X.; Cheung W.-M.; So Y.-M.; Chong M.-C.; Sung H. H. Y.; Williams I. D.; Lin Z.; Leung W.-H. 4-Coordinated, 14-Electron Ruthenium(II) Chalcogenolate Complexes: Synthesis, Electronic Structure and Reactions with PhICl2 and organic azides. Dalton Trans. 2019, 48, 13315–13325..
Not in our library10.1039/c9dt02457c
297.
Barnett H. J.; Hill A. F. Halogenation of A-frame μ-Carbido Complexes: a Diamagnetic Rhodium(II) Carbido Complex. Chem. Commun. 2020, 56, 7738–7740..
Not in our library10.1039/d0cc02349c
298.
Parker G. L.; Lau S.; Leforestier B.; Chaplin A. B. Probing the Donor Properties of Pincer Ligands Using Rhodium Carbonyl Fragments: An Experimental and Computational Case Study. Eur. J. Inorg. Chem. 2019, 2019, 3791–3798..
Not in our library10.1002/ejic.201900727
299.
Zhang L.-L.; Zhang L.; Li S.-J.; Fang D.-C. DFT Studies on the Distinct Mechanisms of C-H Activation and Oxidation Reactions Mediated by Mononuclear- and Binuclear-Palladium. Dalton Trans. 2018, 47, 6102–6111..
Not in our library10.1039/c8dt00236c
300.
Gruenwald A.; Orth N.; Scheurer A.; Heinemann F. W.; Poethig A.; Munz D. An Isolable Terminal Imido Complex of Palladium and Catalytic Implications. Angew. Chem., Int. Ed. 2018, 57, 16228–16232..
Not in our library10.1002/anie.201809152
301.
Sanz C. A.; McKay Z. R.; MacLean S. W. C.; Patrick B. O.; Hicks R. G. Synthesis and Redox Reactions of bis(Verdazyl)palladium Complexes. Dalton Trans. 2017, 46, 12636–12644..
Not in our library10.1039/c7dt02646c
302.
Sahu S.; Gabbai F. P. Photoreductive Elimination of Chlorine from Antimony in an [SbPd]VII Complex. J. Am. Chem. Soc. 2017, 139, 5035–5038..
Not in our library10.1021/jacs.7b01977
303.
Li Y.-Z.; Ganguly R.; Leong W. K. Oxidative Addition of Halogen Across an Os-Os or Os-Sb Bond: Formation of Five-Membered Osmium-Antimony Carbonyl Rings. J. Organomet. Chem. 2016, 811, 66–73..
Not in our library10.1016/j.jorganchem.2016.03.025
304.
Ng R.; Cheng S.-C.; Chan K.-L.; Leung C.-P.; Cheung W.-M.; Sung H. H. Y.; Lee H. K.; Ko C.-C.; Williams I. D.; Lin Z.; Leung W.-H. High-Valent Iridium Complexes Containing a Tripodal Bis-Cyclometalated C∧N∧C Ligand. Organometallics 2023, 42, 719–731..
Not in our library10.1021/acs.organomet.3c00100
305.
Do T. H.; Brown S. N. Mono- and Bis(iminoxolene)iridium Complexes: Synthesis and Covalency in π Bonding. Inorg. Chem. 2022, 61, 5547–5562..
Not in our library10.1021/acs.inorgchem.1c04005
306.
Danopoulos A. A.; Braunstein P.; Sassmannshausen J.; Pugh D.; Wright J. A. ″Pincer″ Pyridine-Dicarbene-Iridium and -Ruthenium Complexes and Derivatives Thereof. Eur. J. Inorg. Chem. 2020, 2020, 3359–3369..
Not in our library10.1002/ejic.202000429
307.
Soto M. A.; Carta V.; Suzana I.; Patrick B. O.; Lelj F.; MacLachlan M. J. Cycling a Tether into Multiple Rings: Pt-Bridged Macrocycles for Differentiated Guest Recognition, Pseudorotaxane Transformations, and Guest Capture and Release. Angew. Chem., Int. Ed. 2023, 62, e202216029.
Not in our library10.1002/anie.202216029
308.
Dikova Y. M.; Yufit D. S.; Williams J. A. G. Platinum(IV) Complexes with Tridentate, NNC-Coordinating Ligands: Synthesis, Structures, and Luminescence. Inorg. Chem. 2023, 62, 1306–1322..
Not in our library10.1021/acs.inorgchem.2c04116
309.
Vivancos A.; Bautista D.; Gonzalez-Herrero P. Phosphorescent Tris-cyclometalated Pt(IV) Complexes with Mesoionic N-Heterocyclic Carbene and 2-Arylpyridine Ligands. Inorg. Chem. 2022, 61, 12033–12042..
Not in our library10.1021/acs.inorgchem.2c02039
310.
Karimi M.; Gabbai F. P. Photoreductive Elimination of PhCl Across the Dinuclear Core of a [GePt]VI Complex. Organometallics 2022, 41, 642–648..
Not in our library10.1021/acs.organomet.2c00004
311.
Karimi M.; Tabei E. S.; Fayad R.; Saber M. R.; Danilov E. O.; Jones C.; Castellano F. N.; Gabbai F. P. Photodriven Elimination of Chlorine From Germanium and Platinum in a Dinuclear PtII→GeIV Complex. Angew. Chem., Int. Ed. 2021, 60, 22352–22358..
Not in our library10.1002/anie.202107485
312.
Lapierre E. A.; Piers W. E.; Lin J.-B.; Gendy C. Synthesis and Structures of Stable PtII and PtIV Alkylidenes: Evidence for π-Bonding and Relativistic Stabilization. Chem. - Eur. J. 2019, 25, 4305–4308..
Not in our library10.1002/chem.201806065
313.
Crespo M.; Font-Bardia M.; Hamidizadeh P.; Martinez M.; Nabavizadeh S. M. Kinetico-mechanistic Study on the Reduction/Complexation Sequence of PtIV/PtII Organometallic Complexes by Thiol-Containing Biological Molecules. Inorg. Chim. Acta 2019, 486, 8–16..
Not in our library10.1016/j.ica.2018.10.021
314.
Chikunov I. E.; Ranny G. S.; Astakhov A. V.; Tafeenko V. A.; Chernyshev V. M. Mechanochemical Synthesis of Platinum(IV) Complexes with N-heterocyclic Carbenes. Russ. Chem. Bull. 2018, 67, 2003–2009..
Not in our library10.1007/s11172-018-2321-2
315.
Belli Dell’Amico D.; Fioco D.; Labella L.; Marchetti F.; Samaritani S. Clean Oxidations by Iodobenzene Dichloride: Platinum(IV) Complexes Containing Triphenylphosphine. Polyhedron 2018, 145, 63–69..
Not in our library10.1016/j.poly.2018.01.033
316.
Shaw P. A.; Clarkson G. J.; Rourke J. P. Oxidation of an o-Tolyl Phosphine Complex of Platinum: C-H Activation and Transcyclometallation. J. Organomet. Chem. 2017, 851, 115–121..
Not in our library10.1016/j.jorganchem.2017.09.026
317.
Puerta Lombardi B. M.; Brown R. M.; Gendy C.; Chang C. Y.; Chivers T.; Roesler R. Nickel and Platinum PCP Pincer Complexes Incorporating an Acyclic Diaminoalkyl Central Moiety Connecting Imidazole or Pyrazole Rings. Organometallics 2017, 36, 3250–3256..
Not in our library10.1021/acs.organomet.7b00396
318.
Shiri F.; Ariafard A. Mechanistic Details for Oxidative Addition of PhICl2 to Gold(I) Complexes. Chem. Commun. 2023, 59, 4668–4671..
Not in our library10.1039/d3cc00543g
319.
Grabicki N.; Fisher S.; Dumele O. A Fourfold Gold(I)-Aryl Macrocycle with Hyperbolic Geometry and its Reductive Elimination to a Carbon Nanoring Host. Angew. Chem., Int. Ed. 2023, 62, e202217917.
Not in our library10.1002/anie.202217917
320.
Wen Z.; Maisonhaute E.; Zhang Y.; Roland S.; Sollogoub M. Janus-Type Homo-, Hetero- and Mixed Valence-Bimetallic Complexes with One Metal Encapsulated in a Cyclodextrin. Chem. Commun. 2022, 58, 4516–4519..
Not in our library10.1039/d2cc00219a
321.
Abe R.; Tsuchido Y.; Ide T.; Koizumi T.-a.; Osakada K. Digold(I) Thianthrenyl Complexes. Effect of Diphosphine Ligands on Molecular Structures in the Solid State and in Solution. ACS Omega 2022, 7, 9594–9601..
Not in our library10.1021/acsomega.1c06938
322.
van der Westhuizen D.; Slabber C. A.; Fernandes M. A.; Joubert D. F.; Kleinhans G.; van der Westhuizen C. J.; Stander A.; Munro O. Q.; Bezuidenhout D. I. A Cytotoxic Bis(1,2,3-triazol-5-ylidene)carbazolide Gold(III) Complex Targets DNA by Partial Intercalation. Chem. - Eur. J. 2021, 27, 8295–8307..
Not in our library10.1002/chem.202100598
323.
Reiersoelmoen A. C.; Battaglia S.; Orthaber A.; Lindh R.; Erdelyi M.; Fiksdahl A. P,N-Chelated Gold(III) Complexes: Structure and Reactivity. Inorg. Chem. 2021, 60, 2847–2855..
Not in our library10.1021/acs.inorgchem.0c02720
324.
Benaissa I.; Gajda K.; Vendier L.; Lugan N.; Kajetanowicz A.; Grela K.; Michelet V.; Cesar V.; Bastin S. An Anionic, Chelating C(sp3)/NHC ligand from the Combination of an N-heterobicyclic Carbene and Barbituric Heterocycle. Organometallics 2021, 40, 3223–3234..
Not in our library10.1021/acs.organomet.1c00458
325.
Tsuchido Y.; Abe R.; Ide T.; Osakada K. A Macrocyclic Gold(I)-Biphenylene Complex: Triangular Molecular Structure with Twisted Au2(diphosphine) Corners and Reductive Elimination of [6]Cycloparaphenylene. Angew. Chem., Int. Ed. 2020, 59, 22928–22932..
Not in our library10.1002/anie.202005482
326.
Levchenko V.; Glessi C.; Oeien-Oedegaard S.; Tilset M. Organometallic Chemistry in Aqua Regia: Metal and Ligand Based Oxidations of (NHC)AuCl Complexes. Dalton Trans. 2020, 49, 3473–3479..
Not in our library10.1039/c9dt04472h
327.
Sun C.; Mirzadeh N.; Guo S.-X.; Li J.; Li Z.; Bond A. M.; Zhang J.; Bhargava S. K. Unprecedented Formation of a Binuclear Au(II)-Au(II) Complex through Redox State Cycling: Electrochemical Interconversion of Au(I)-Au(I), Au(II)-Au(II), and Au(I)-Au(III) in Binuclear Complexes Containing the Carbanionic Ligand C6F4PPh2. Inorg. Chem. 2019, 58, 13999–14004..
Not in our library10.1021/acs.inorgchem.9b01983
328.
Srinivasa Reddy T.; Priver S. H.; Rao V. V.; Mirzadeh N.; Bhargava S. K. Gold(I) and Gold(III) Phosphine Complexes: Synthesis, Anticancer Activities Towards 2D And 3D Cancer Models, and Apoptosis Inducing Properties. Dalton Trans. 2018, 47, 15312–15323..
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Anumandla D.; Acharya A.; Jeffrey C. S. Oxidative [3 + 2] Cycloaddition Reactions of Diaza-Oxyallyl Cationic Intermediates and Indoles for the Synthesis of Imidazoloindolines. Org. Lett. 2016, 18, 476–479..
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419.
Rao Kovvuri V. R.; Xue H.; Romo D. Generation and Reactivity of 2-Amido-1,3-diaminoallyl Cations: Cyclic Guanidine Annulations via Net [3 + 2] and [4 + 3] Cycloadditions. Org. Lett. 2020, 22, 1407–1413..
Not in our library10.1021/acs.orglett.0c00019
420.
Singh S. J.; Devi N. S. Diacetoxyiodobenzene Mediated Oxidative Transformation of Thione to Disulfides. Tetrahedron Lett. 2016, 57, 5941–5943..
Not in our library10.1016/j.tetlet.2016.11.091
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Singh S. J.; Devi N. S. Diacetoxyiodobenzene Mediated Oxidative Dethionation of N-Substituted 5-Arylmethylidene Rhodanines: an Efficient Synthesis of N-Substituted 5-Arylmethylidene Thiazolidine-2,4-Diones. ARKIVOC 2017, 2017 (iv), 137–144..
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Srisa J.; Tankam T.; Sukwattanasinitt M.; Wacharasindhu S. Micelle-Enabled One-Pot Guanidine Synthesis in Water Directly from Isothiocyanate using Hypervalent Iodine(III) Reagents under Mild Conditions. Chem. - Asian J. 2019, 14, 3335–3343..
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Nahakpam L.; Chipem F. A. S.; Chingakham B. S.; Laitonjam W. S. Diacetoxyiodobenzene Assisted C-O Bond Formation via Sequential Acylation and Deacylation Process: Synthesis of Benzoxazole Amides and their Mechanistic Study by DFT. Org. Biomol. Chem. 2016, 14, 7735–7745..
Not in our library10.1039/c6ob00968a
424.
Hu Z.-C.; Wu Y.-X.; Ye L.; Cui J.-J.; Dong Z.-B. An Efficient and Practical Construction of S-N Bond from Aryl Thioureas and Amines under Metal-Free Conditions. Eur. J. Org. Chem. 2022, 2022, e202200419.
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Zhang Z.-X.; Bell C.; Ding M.; Willis M. C. Modular Two-Step Route to Sulfondiimidamides. J. Am. Chem. Soc. 2022, 144, 11851–11858..
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Marzag H.; Schuler M.; Tatibouet A.; Reboul V. Synthesis of Methionine-Derived Endocyclic Sulfilimines and Sulfoximines. Eur. J. Org. Chem. 2017, 2017, 896–900..
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Shao Q.; Li H.-s.; Xiao Y.-l.; Li Y.; Zhao L.-j.; Ren X.-f.; Liu Y.; Liu J.-q. Facile Preparation of Nitroguanidines Containing a Sulfoximine Motif. Tetrahedron Lett. 2020, 61, 151450.
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Ding M.; Zhang Z.-X.; Davies T. Q.; Willis M. C. A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides. Org. Lett. 2022, 24, 1711–1715..
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429.
Lu X.; Huang G.; Ye J.; Bashir M. A.; Su J.; Yang K.; Liang F.; Xu X. Hypervalent Iodine-Mediated Synthesis of Sulfinimidate Esters from Sulfenamides. Org. Lett. 2023, 25, 2151–2156..
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430.
Maloney T. P.; Berman J. L.; Michael F. E. Metal-Free Allylic C-H Amination of Vinylsilanes and Vinylboronates using Silicon or Boron as a Regioselectivity Switch. Angew. Chem., Int. Ed. 2022, 61, e202210109.
Not in our library10.1002/anie.202210109
431.
Liu Y.; Chen Z.-H.; Li Y.; Qian J.; Li Q.; Wang H. Boryl-Dictated Site-Selective Intermolecular Allylic and Propargylic C-H Amination. J. Am. Chem. Soc. 2022, 144, 14380–14387..
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432.
Obenschain D. C.; Tabor J. R.; Michael F. E. Metal-Free Intermolecular Allylic C-H Amination of Alkenes Using Primary Carbamates. ACS Catal. 2023, 13, 4369–4375..
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433.
Nakamura A.; Tanaka S.; Imamiya A.; Takane R.; Ohta C.; Fujimura K.; Maegawa T.; Miki Y. Synthesis of 3-Acylindoles by Oxidative Rearrangement of 2-Aminochalcones Using a Hypervalent Iodine Reagent and Cyclization Sequence. Org. Biomol. Chem. 2017, 15, 6702–6705..
Not in our library10.1039/c7ob01536d
434.
Tian G.; Fedoseev P.; Van der Eycken E. V. Hypervalent Iodine(III)-Mediated Cascade Cyclization of Propargylguanidines and Total Syntheses of Kealiinine B and C. Chem. - Eur. J. 2017, 23, 5224–5227..
Not in our library10.1002/chem.201700934
435.
Chavan S. S.; Rupanawar B. D.; Kamble R. B.; Shelke A. M.; Suryavanshi G. Metal-free Annulation of β-Acylamino Ketones: Facile Access to Spirooxazolines and Oxazolines via Oxidative C-O Bond Formation. Org. Chem. Front. 2018, 5, 544–548..
Not in our library10.1039/c7qo00783c
436.
Zhao C.-Y.; Li K.; Pang Y.; Li J.-Q.; Liang C.; Su G.-F.; Mo D.-L. Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles. Adv. Synth. Catal. 2018, 360, 1919–1925..
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437.
Zhou Y.; Li D.; Tang S.; Sun H.; Huang J.; Zhu Q. PhI(OAc)2-Mediated Dearomative C-N Coupling: Facile Construction of the Spiro[Indoline-3,2’-Pyrrolidine] Skeleton. Org. Biomol. Chem. 2018, 16, 2039–2042..
Not in our library10.1039/c8ob00343b
438.
Sun J.; Li G.; Zhang G.; Cong Y.; An X.; Zhang-Negrerie D.; Du Y. Cascade Formation of C3-Unsymmetric Spirooxindoles via PhI(OAc)2-Mediated Oxidative C-C/C-N Bond Formation. Adv. Synth. Catal. 2018, 360, 2476–2481..
Not in our library10.1002/adsc.201800314
439.
Chen H.-L.; Wei D.; Zhang J.-W.; Li C.-L.; Yu W.; Han B. Synthesis of Halomethyl Isoxazoles/Cyclic Nitrones via Cascade Sequence: 1,2-Halogen Radical Shift as a Key Link. Org. Lett. 2018, 20, 2906–2910..
Not in our library10.1021/acs.orglett.8b00967
440.
Fan H.; Pan P.; Zhang Y.; Wang W. Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature. Org. Lett. 2018, 20, 7929–7932..
Not in our library10.1021/acs.orglett.8b03503
441.
Xing Q.; Liang H.; Bao M.; Li X.; Zhang J.; Bi T.; Zhang Y.; Xu J.; Du Y.; Zhao K. Metal-free Synthesis of Spiro-2,2’-benzo[b]furan-3,3′-ones via PhI(OAc)2-Mediated Cascade Spirocyclization. Adv. Synth. Catal. 2019, 361, 4669–4673..
Not in our library10.1002/adsc.201900652
442.
Duddupudi A. L.; Pandey P.; Vo H.; Welsh C. L.; Doerksen R. J.; Cuny G. D. Hypervalent Iodine Mediated Oxidative Cyclization of Acrylamide N-Carbamates to 5,5-Disubstituted Oxazolidine-2,4-Diones. J. Org. Chem. 2020, 85, 7549–7557..
Not in our library10.1021/acs.joc.0c00581
443.
Xu K.; Yang S.; Ding Z. PhI(OAc)2-Mediated Oxidative Rearrangement of Allylic Amides: Efficient Synthesis of Oxazoles and β-Keto Amides. Org. Chem. Front. 2020, 7, 69–72..
Not in our library10.1039/c9qo01298b
444.
Wang Q.-B.; Tang S.; Wang Y.-J.; Yuan Y.; Chen T.; Jia A.-Q. PhI(OAc)2-Mediated Intramolecular Oxidative C-N Coupling and Detosylative Aromatization: an Access to Indolo[2,3-b]quinolines. RSC Adv. 2021, 11, 17206–17211..
Not in our library10.1039/d1ra01894a
445.
Wang Y.; He Q.; Fan R. Facile Synthesis of 4-Acetoxyindoles via PhI(OAc)2-Mediated Dearomatization of 2-Alkynylanilines. Org. Chem. Front. 2021, 8, 3004–3007..
Not in our library10.1039/d1qo00358e
446.
Tang P.; Wen L.; Ma H.-J.; Yang Y.; Jiang Y. Synthesis of Acyloxy-2H-Azirine and Sulfonyloxy-2H-Azirine Derivatives via a One-Pot Reaction of β-Enamino Esters, PIDA and Carboxylic Acid or Sulfonic Acid. Org. Biomol. Chem. 2022, 20, 3061–3066..
Not in our library10.1039/d2ob00364c
447.
Chen X.; Shen Y.-T.; Zhao Z.-W.; Hou Y.-J.; Sun B.-X.; Fan T.-G.; Li Y.-M. Oxy-/Amino-Difluoromethylthiolation of Alkenes: Synthesis of HCF2S-Containing Isoxazolines and Pyrazolines. Adv. Synth. Catal. 2022, 364, 3193–3198..
Not in our library10.1002/adsc.202200672
448.
Song L.-R.; Li H.; Wang S.-F.; Lin J.-P.; Huang B.; Long Y.-Q. Metal-Free Hypervalent Iodine-Promoted Tandem Carbonyl Migration and Unactivated C(Ph)-C(Alkyl) Bond Cleavage for Quinolone Scaffold Synthesis. Chem. Commun. 2022, 58, 8340–8343..
Not in our library10.1039/d2cc02245a
449.
Shinde R. S.; Narnawre A. R.; Walke P. M.; Karade N. N. (Diacetoxyiodo)benzene Mediated Oxidative Conversion of Erlenmeyer Azlactones to 2-Substituted Oxazolines Under Basic Conditions: Synthesis of 4-Methoxy-2-phenyl-5-aryl-4,5-dihydrooxazole-4-carboxylate. ChemistrySelect 2023, 8, e202203899.
Not in our library10.1002/slct.202203899
450.
Izquierdo S.; Essafi S.; del Rosal I.; Vidossich P.; Pleixats R.; Vallribera A.; Ujaque G.; Lledos A.; Shafir A. Acid Activation in Phenyliodine Dicarboxylates: Direct Observation, Structures, and Implications. J. Am. Chem. Soc. 2016, 138, 12747–12750..
Not in our library10.1021/jacs.6b07999
451.
Izquierdo S.; Bouvet S.; Wu Y.; Molina S.; Shafir A. The Coming of Age in Iodane-Guided ortho-C-H Propargylation: From Insight to Synthetic Potential. Chem. - Eur. J. 2018, 24, 15517–15521..
Not in our library10.1002/chem.201804058
452.
Tian J.; Luo F.; Zhang C.; Huang X.; Zhang Y.; Zhang L.; Kong L.; Hu X.; Wang Z.-X.; Peng B. Selective ortho C-H Cyanoalkylation of (Diacetoxyiodo)arenes through [3,3]-Sigmatropic Rearrangement. Angew. Chem., Int. Ed. 2018, 57, 9078–9082..
Not in our library10.1002/anie.201803455
453.
Huang X.; Zhang Y.; Zhang C.; Zhang L.; Xu Y.; Kong L.; Wang Z.-X.; Peng B. The ortho Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect. Angew. Chem., Int. Ed. 2019, 58, 5956–5961..
Not in our library10.1002/anie.201900745
454.
Zhao W.; Huang X.; Zhan Y.; Zhang Q.; Li D.; Zhang Y.; Kong L.; Peng B. Dearomative Dual Functionalization of Aryl Iodanes. Angew. Chem., Int. Ed. 2019, 58, 17210–17214..
Not in our library10.1002/anie.201909019
455.
Chen W. W.; Cunillera A.; Chen D.; Lethu S.; Lopez de Moragas A.; Zhu J.; Sola M.; Cuenca A. B.; Shafir A. Iodane-Guided ortho C-H Allylation. Angew. Chem., Int. Ed. 2020, 59, 20201–20207..
Not in our library10.1002/anie.202009369
456.
Tian J.; Luo F.; Zhang Q.; Liang Y.; Li D.; Zhan Y.; Kong L.; Wang Z.-X.; Peng B. Asymmetric Iodonio-[3,3]-Sigmatropic Rearrangement to Access Chiral α-Aryl Carbonyl Compounds. J. Am. Chem. Soc. 2020, 142, 6884–6890..
Not in our library10.1021/jacs.0c00783
457.
Zhang L.; Bao W.; Liang Y.; Pan W.; Li D.; Kong L.; Wang Z.-X.; Peng B. Morita-Baylis-Hillman-Type [3,3]-Rearrangement: Switching from Z- to E-Selective α-Arylation by New Rearrangement Partners. Angew. Chem., Int. Ed. 2021, 60, 11414–11422..
Not in our library10.1002/anie.202100497
458.
Du P.; Zhou L.; Zhang Z.; Huang X.; Peng B. Aromatic Iodonium/Sulfonium Rearrangement Using Difluoroenol Silyl Ethers. Phosphorus, Sulfur Silicon Relat. Elem. 2023, 198, 481–485..
Not in our library10.1080/10426507.2022.2113977
459.
Mowdawalla C.; Ahmed F.; Li T.; Pham K.; Dave L.; Kim G.; Hyatt I. F. D. Hypervalent Iodine-Guided Electrophilic Substitution: para-Selective Substitution Across Aryl Iodonium Compounds with Benzyl Groups. Beilstein J. Org. Chem. 2018, 14, 1039–1045..
Not in our library10.3762/bjoc.14.91
460.
Wu Y.; Bouvet S.; Izquierdo S.; Shafir A. Synthesis of Polysubstituted Iodoarenes Enabled by Iterative Iodine-Directed para and ortho C-H Functionalization. Angew. Chem., Int. Ed. 2019, 58, 2617–2621..
Not in our library10.1002/anie.201809657
461.
Sousa e Silva F. C.; Van N. T.; Wengryniuk S. E. Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents. J. Am. Chem. Soc. 2020, 142, 64–69..
Not in our library10.1021/jacs.9b11282
462.
Hori M.; Guo J.-D.; Yanagi T.; Nogi K.; Sasamori T.; Yorimitsu H. Sigmatropic Rearrangements of Hypervalent-Iodine-Tethered Intermediates for the Synthesis of Biaryls. Angew. Chem., Int. Ed. 2018, 57, 4663–4667..
Not in our library10.1002/anie.201801132
463.
Arava S.; Santra S. K.; Pathe G. K.; Kapanaiah R.; Szpilman A. M. Direct Umpolung Morita-Baylis-Hillman like α-Functionalization of Enones via Enolonium Species. Angew. Chem., Int. Ed. 2020, 59, 15171–15175..
Not in our library10.1002/anie.202005286
464.
Martins B. S.; Kaiser D.; Bauer A.; Tiefenbrunner I.; Maulide N. Formal Enone α-Arylation via I(III)-Mediated Aryl Migration/Elimination. Org. Lett. 2021, 23, 2094–2098..
Not in our library10.1021/acs.orglett.1c00251
465.
Wang Y.; Wang Y.; Guo Z.; Zhang Q.; Li D. Metal-Free Oxidative C-H Amination of 8-Acylaminoquinolines and Anilides with N-Fluorobenzenesulfonimide. Asian J. Org. Chem. 2016, 5, 1438–1441..
Not in our library10.1002/ajoc.201600389
466.
Wang G.; Han J.; Wang K.; Li H.; Duan G.; Xia C.; Li F. Methoxylation on the C5 and C6 Positions of Quinolines with Methanol. Catal. Commun. 2018, 114, 37–41..
Not in our library10.1016/j.catcom.2018.05.021
467.
Thrimurtulu N.; Dey A.; Pal K.; Nair A.; Kumar S.; Volla C. M. R. Metal-Free Remote C-H Bond Acetoxylation of 8-Aminoquinolines on the C5-Position. ChemistrySelect 2017, 2, 7251–7254..
Not in our library10.1002/slct.201701388
468.
Wang Y.; Wang Y.; Zhang Q.; Li D. Site-Selective Oxidative C-H Sulfonylation of 8-Acylaminoquinolines and Anilides under Metal-Free Conditions. Org. Chem. Front. 2017, 4, 514–518..
Not in our library10.1039/c6qo00730a
469.
Mondal S.; Hajra A. Metal-Free C-5 Hydroxylation of 8-Aminoquinoline Amide. J. Org. Chem. 2018, 83, 11392–11398..
Not in our library10.1021/acs.joc.8b01635
470.
Xia C.; Wang K.; Xu J.; Shen C.; Sun D.; Li H.; Wang G.; Zhang P. Selective Remote Esterification of 8-Aminoquinoline Amides via Copper(II)-Catalyzed C(sp2)-O Cross-Coupling Reaction. Org. Biomol. Chem. 2017, 15, 531–535..
Not in our library10.1039/c6ob02375d
471.
Wu C.; Zhou H.; Wu Q.; He M.; Li P.; Su Q.; Mu Y. Copper-Catalyzed Regioselective C-H Iodination of Aromatic Carboxamides. Synlett 2016, 27, 868–875..
Not in our library10.1055/s-0035-1561335
472.
Mondal S.; Samanta S.; Jana S.; Hajra A. (Diacetoxy)iodobenzene-Mediated Oxidative C-H Amination of Imidazopyridines at Ambient Temperature. J. Org. Chem. 2017, 82, 4504–4510..
Not in our library10.1021/acs.joc.7b00564
473.
Kumar R.; Rawat D.; Adimurthy S. Polyethylene Glycol (PEG-400) as Methylene Spacer and Green Solvent for the Synthesis of Heterodiarylmethanes under Metal-Free Conditions. Eur. J. Org. Chem. 2020, 2020, 3499–3507..
Not in our library10.1002/ejoc.202000467
474.
Mondal S.; Samanta S.; Singsardar M.; Hajra A. Aminomethylation of Imidazoheterocycles with Morpholine. Org. Lett. 2017, 19, 3751–3754..
Not in our library10.1021/acs.orglett.7b01594
475.
Luan N.; Liu Z.; Han S.; Shen L.; Li J.; Zou D.; Wu Y.; Wu Y. PhI(OAc)2-Mediated Oxidative C-H Sulfoximination of Imidazopyridines under Mild Conditions. Tetrahedron Lett. 2020, 61, 151362.
Not in our library10.1016/j.tetlet.2019.151362
476.
(Diacetoxy)iodobenzene-Mediated Regioselective Imidation of Imidazoheterocycles with N‑Fluorobenzenesulfonimide · 2018
Not checked
477.
Han S.; Gao X.; Wu Q.; Li J.; Zou D.; Wu Y.; Wu Y. Transition-Metal-Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions. Adv. Synth. Catal. 2019, 361, 1559–1563..
Not in our library10.1002/adsc.201801541
478.
Murugan A.; Babu V. N.; Polu A.; Sabarinathan N.; Bakthadoss M.; Sharada D. S. Regioselective C3-H Trifluoromethylation of 2H-Indazole under Transition-Metal-Free Photoredox Catalysis. J. Org. Chem. 2019, 84, 7796–7803..
Not in our library10.1021/acs.joc.9b00676
479.
Indukuri D. R.; Potuganti G. R.; Alla M. Hypervalent Iodine Mediated Efficient Solvent-Free Regioselective Halogenation and Thiocyanation of Fused N-Heterocycles. Synlett 2019, 30, 1573–1579..
Not in our library10.1055/s-0037-1611856
480.
Patel O. P. S.; Jaspal S.; Shinde V. N.; Nandwana N. K.; Rangan K.; Kumar A. Phenyliodine(III) Diacetate-Mediated 1,2-ipso-Migration in Mannich Bases of Imidazo[1,2-a]pyridines: Preparation of N-Acetoxymethyl/Alkoxymethyl-N-arylimidazo[1,2-a]pyridine-3-amines. J. Org. Chem. 2020, 85, 7309–7321..
Not in our library10.1021/acs.joc.0c00674
481.
Kumar R.; Rawat D.; Semwal R.; Badhani G.; Adimurthy S. Hypervalent Iodine Mediated Synthesis of Imidazo[1,2-a]pyridine Ethers: Consecutive Methylene Linkage and Insertion of Ethylene Glycol. New J. Chem. 2021, 45, 7491–7495..
Not in our library10.1039/d1nj00657f
482.
Zhu Y.-S.; Xue Y.; Liu W.; Zhu X.; Hao X.-Q.; Song M.-P. Temperature-Controlled Chalcogenation and Chalcogenocyanation of Imidazopyridines in Water under Transition Metal-Free Conditions. J. Org. Chem. 2020, 85, 9106–9116..
Not in our library10.1021/acs.joc.0c01035
483.
Xue W.; Su Y.; Wang K.-H.; Cao L.; Feng Y.; Zhang W.; Huang D.; Hu Y. Phenyliodonium Diacetate Mediated Carbotrifluoromethylation of Quinoxalin-2(1H)-ones. Asian J. Org. Chem. 2019, 8, 887–892..
Not in our library10.1002/ajoc.201900118
484.
Wimonsong W.; Yotphan S. PIDA-Induced Oxidative C-N Bond Coupling of Quinoxalinones and Azoles. Tetrahedron 2021, 81, 131919.
Not in our library10.1016/j.tet.2020.131919
485.
Mali N.; Ibarra-Gutierrez J. G.; Lugo Fuentes L. I.; Ortiz-Alvarado R.; Chacon-Garcia L.; Navarro-Santos P.; Jimenez-Halla J. O. C.; Solorio-Alvarado C. R. Iodine(III)-Mediated Free-Aniline Iodination through Acetyl Hypoiodite Formation: Study of the Reaction Pathway. Eur. J. Org. Chem. 2022, 2022, e202201067.
Not in our library10.1002/ejoc.202201067
486.
Wang H.; Frings M.; Bolm C. Halocyclizations of Unsaturated Sulfoximines. Org. Lett. 2016, 18, 2431–2434..
Not in our library10.1021/acs.orglett.6b00958
487.
Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system · 2018
Not checked
488.
Satkar Y.; Ramadoss V.; Nahide P. D.; Garcia-Medina E.; Juarez-Ornelas K. A.; Alonso-Castro A. J.; Chavez-Rivera R.; Jimenez-Halla J. O. C.; Solorio-Alvarado C. R. Practical, Mild and Efficient Electrophilic Bromination of Phenols by a New I(III)-based Reagent: the PIDA-AlBr3 System. RSC Adv. 2018, 8, 17806–17812..
Not in our library10.1039/c8ra02982b
489.
Himabindu V.; Parvathaneni S. P.; Rao V. J. PhI(OAc)2/NaX-Mediated Halogenation Providing Access to Valuable Synthons 3-Haloindole Derivatives. New J. Chem. 2018, 42, 18889–18893..
Not in our library10.1039/c8nj03822h
490.
Mao Z.; Liu M.; Zhu G.; Zhou J.; Zhang X. Transition-Metal-Free Highly Regioselective C-H Acetoxylation of Pyrrolo[2,3-d]pyrimidine Derivatives. Org. Chem. Front. 2020, 7, 2696–2702..
Not in our library10.1039/d0qo00702a
491.
Bian H.-L.; Tang S.-Z.; Chen M.-E.; Zhang X.-M.; Lv J.-W.; Chen X.-W.; Qi F.-M.; Chen S.-W.; Zhang F.-M. Transition-Metal-Free Site-Selective γ-C(sp2)-H Monoiodination of Arenes Directed by an Aliphatic Keto Group. Org. Lett. 2020, 22, 5314–5319..
Not in our library10.1021/acs.orglett.0c01466
492.
Watanabe A.; Koyamada K.; Miyamoto K.; Kanazawa J.; Uchiyama M. Decarboxylative Bromination of Sterically Hindered Carboxylic Acids with Hypervalent Iodine(III) Reagents. Org. Process Res. Dev. 2020, 24, 1328–1334..
Not in our library10.1021/acs.oprd.0c00130
493.
Liu J.; Liu Q.-Y.; Fang X.-X.; Liu G.-Q.; Ling Y. Preparation of Polysubstituted Dihydrofurans through a PhI(OAc)2-Promoted Haloenolcyclization of Olefinic Dicarbonyl Compounds. Org. Biomol. Chem. 2018, 16, 7454–7460..
Not in our library10.1039/c8ob02161a
494.
Peilleron L.; Grayfer T. D.; Dubois J.; Dodd R. H.; Cariou K. Iodine(III)-Mediated Halogenations of Acyclic Monoterpenoids. Beilstein J. Org. Chem. 2018, 14, 1103–1111..
Not in our library10.3762/bjoc.14.96
495.
Lin X.-L.; Yu Y.; Zhang L.; Leng L.-J.; Xiao D.-R.; Cai T.; Luo Q.-L. Switchable synthesis of 1,4-Bridged Dihydroisoquinoline-3-ones and Isoquinoline-1,3,4-triones through Radical Oxidation of Isoquinolinium Salts with Phenyliodine(III) Diacetate. Org. Chem. Front. 2022, 9, 4676–4684..
Not in our library10.1039/d2qo00887d
496.
Yi W.; Liu Q.-Y.; Fang X.-X.; Lou S.-C.; Liu G.-Q. Preparation of Oxazolines and Oxazoles via a PhI(OAc)2-Promoted Cyclization of N-Propargylamides. Org. Biomol. Chem. 2018, 16, 7012–7018..
Not in our library10.1039/c8ob01474d
497.
Dong M.; Wang D.; Tong X. PhI(OAc)2-Mediated Dihalogenative Cyclization of 1,6-Enyne with Lithium Halide. Org. Lett. 2021, 23, 3588–3592..
Not in our library10.1021/acs.orglett.1c00987
498.
Kitamura T.; Morita K.; Nakamori H.; Oyamada J. Synthesis of [1]Benzothieno[3,2-b][1]benzothiophene Derivatives via Successive Iodocyclization/Photocyclization of Alkynes. J. Org. Chem. 2019, 84, 4191–4199..
Not in our library10.1021/acs.joc.9b00213
499.
Liu Y.; Huang D.; Huang J.; Maruoka K. Hypervalent Iodine Mediated Chemoselective Iodination of Alkynes. J. Org. Chem. 2017, 82, 11865–11871..
Not in our library10.1021/acs.joc.7b01555
500.
Rao D. S.; Reddy T. R.; Kashyap S. Chemoselective and Stereospecific Iodination of Alkynes Using Sulfonium Iodate(I) Salt. Org. Biomol. Chem. 2018, 16, 1508–1518..
Not in our library10.1039/c7ob03076b
501.
Payne J. L.; Deng Z.; Flach A. L.; Johnston J. N. Enantioselective Iodolactonization to Prepare ε-Lactone Rings using Hypervalent Iodine. Chem. Sci. 2022, 13, 7318–7324..
Not in our library10.1039/d2sc01587k
502.
Atmuri N. D. P.; Reilley D. J.; Lubell W. D. Peptidomimetic Synthesis by Way of Diastereoselective Iodoacetoxylation and Transannular Amidation of 7–9-Membered Lactams. Org. Lett. 2017, 19, 5066–5069..
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503.
Atmuri N. D. P.; Lubell W. D. Stereo- and Regiochemical Transannular Cyclization of a Common Hexahydro-1H-azonine to Afford Three Different Indolizidinone Dipeptide Mimetics. J. Org. Chem. 2020, 85, 1340–1351..
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504.
Kiyokawa K.; Watanabe T.; Fra L.; Kojima T.; Minakata S. Hypervalent Iodine(III)-Mediated Decarboxylative Ritter-Type Amination Leading to the Production of α-Tertiary Amine Derivatives. J. Org. Chem. 2017, 82, 11711–11720..
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505.
Hypervalent iodine(III)-mediated decarboxylative acetoxylation at tertiary and benzylic carbon centers · 2018
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506.
Kanyiva K. S.; Marina T.; Nishibe S.; Shibata T. Metal-Free Aminoiodination of Alkynes Under Visible Light Irradiation for the Construction of a Nitrogen-Containing Eight-Membered Ring System. Adv. Synth. Catal. 2021, 363, 2746–2751..
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507.
Zeng Y.-F.; Liu X.-G.; Tan D.-H.; Fan W.-X.; Li Y.-N.; Guo Y.; Wang H. Halohydroxylation of Alkenyl MIDA Boronates: Switchable Stereoselectivity Induced by B(MIDA) Substituent. Chem. Commun. 2020, 56, 4332–4335..
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508.
Yang F.; Wang X.; Zhao W.; Yu F.; Yu Z. Hypervalent Iodine(III)-Promoted C3-H Regioselective Halogenation of 4-Quinolones under Mild Conditions. ACS Omega 2021, 6, 34044–34055..
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509.
Bosnidou A. E.; Muniz K. Intermolecular Radical C(sp3)-H Amination under Iodine Catalysis. Angew. Chem., Int. Ed. 2019, 58, 7485–7489..
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Hopkins M. D.; Ozmer G. L.; Witt R. C.; Brandeburg Z. C.; Rogers D. A.; Keating C. E.; Petcoff P. L.; Sheaff R. J.; Lamar A. A. PhI(OAc)2 and Iodine-Mediated Synthesis of N-Alkyl Sulfonamides Derived from Polycyclic Aromatic Hydrocarbon Scaffolds and Determination of their Antibacterial and Cytotoxic Activities. Org. Biomol. Chem. 2021, 19, 1133–1144..
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511.
Griggs S. D.; Martin-Roncero A.; Nelson A.; Marsden S. P. Regioselective Side-Chain Amination of 2-Alkyl Azacycles by Radical Translocation: Total Synthesis of Tetraponerine T8. Chem. Commun. 2021, 57, 919–922..
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Martinez C.; Bosnidou A. E.; Allmendinger S.; Muniz K. Towards Uniform Iodine Catalysis: Intramolecular C-H Amination of Arenes under Visible Light. Chem. - Eur. J. 2016, 22, 9929–9932..
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Gao Y.; Zhao Q.; Li L.; Ma Y.-N. Synthesis of Six-Membered N-Heterocycle Frameworks Based on Intramolecular Metal-Free N-Centered Radical Chemistry. Chem. Rec. 2022, 22, e202100218.
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514.
Li L.; Li Y.; Zhao Z.; Luo H.; Ma Y.-N. Facial Syntheses of Bromobenzothiazines via Catalyst-Free Tandem C-H Amination/Bromination in Water. Org. Lett. 2019, 21, 5995–5999..
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515.
Gao Y.; Jing Y.; Li L.; Zhang J.; Chen X.; Ma Y.-N. Synthesis of Phenanthridines through Iodine-Supported Intramolecular C-H Amination and Oxidation under Visible Light. J. Org. Chem. 2020, 85, 12187–12198..
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516.
Zhang D.; Wang H.; Cheng H.; Hernandez J. G.; Bolm C. An Iodine-Mediated Hofmann-Loeffler-Freytag Reaction of Sulfoximines Leading to Dihydroisothiazole Oxides. Adv. Synth. Catal. 2017, 359, 4274–4277..
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517.
Du W.; Huang H.; Xiao T.; Jiang Y. Metal-Free, Visible-Light Promoted Intramolecular Azole C-H Bond Amination Using Catalytic Amount of I2: A Route to 1,2,3-Triazolo[1,5-a]quinazolin-5(4H)-ones. Adv. Synth. Catal. 2020, 362, 5124–5129..
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Wappes E. A.; Fosu S. C.; Chopko T. C.; Nagib D. A. Triiodide-mediated δ-Amination of Secondary C-H Bonds. Angew. Chem., Int. Ed. 2016, 55, 9974–9978..
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Shaw M.; Kumar A. Visible-Light-Mediated β-C(sp3)-H Amination of Glycosylimidates: En Route to Oxazoline-Fused/Spiro Nonclassical Bicyclic Sugars. Org. Lett. 2019, 21, 3108–3113..
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520.
Kumar Y.; Jaiswal Y.; Kumar A. Visible-Light-Mediated Remote γ-C(sp3)-H Functionalization of Alkylimidates: Synthesis of 4-Iodo-3,4-dihydropyrrole Derivatives. Org. Lett. 2018, 20, 4964–4969..
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Wappes E. A.; Nakafuku K. M.; Nagib D. A. Directed β C-H Amination of Alcohols via Radical Relay Chaperones. J. Am. Chem. Soc. 2017, 139, 10204–10207..
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Wappes E. A.; Vanitcha A.; Nagib D. A. β C-H di-Halogenation via Iterative Hydrogen Atom Transfer. Chem. Sci. 2018, 9, 4500–4504..
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Stateman L. M.; Wappes E. A.; Nakafuku K. M.; Edwards K. M.; Nagib D. A. Catalytic β C-H Amination via an Imidate Radical Relay. Chem. Sci. 2019, 10, 2693–2699..
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Chen A. D.; Herbort J. H.; Wappes E. A.; Nakafuku K. M.; Mustafa D. N.; Nagib D. A. Radical Cascade Synthesis of Azoles via Tandem Hydrogen Atom Transfer. Chem. Sci. 2020, 11, 2479–2486..
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525.
Prusinowski A. F.; Twumasi R. K.; Wappes E. A.; Nagib D. A. Vicinal, Double C-H Functionalization of Alcohols via an Imidate Radical-Polar Crossover Cascade. J. Am. Chem. Soc. 2020, 142, 5429–5438..
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526.
Koesel T.; Schulz G.; Draeger G.; Kirschning A. Photochemical Transformations with Iodine Azide after Release from an Ion-Exchange Resin. Angew. Chem., Int. Ed. 2020, 59, 12376–12380..
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527.
Schulz G.; George V.; Taser D.; Kirschning A. Taming Bromine Azide for use in Organic Solvents-Radical Bromoazidations and Alcohol Oxidations. J. Org. Chem. 2023, 88, 3781–3786..
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528.
Koesel T.; Draeger G.; Kirschning A. Oxidative Azidations of Phenols and Ketones Using Iodine Azide after Release from an Ion Exchange Resin. Org. Biomol. Chem. 2021, 19, 2907–2911..
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529.
Meyer C. F.; Hell S. M.; Misale A.; Trabanco A. A.; Gouverneur V. Hydrodifluoromethylation of Alkenes with Difluoroacetic Acid. Angew. Chem., Int. Ed. 2019, 58, 8829–8833..
Not in our library10.1002/anie.201903801
530.
Guo C.; Han X.; Feng Y.; Liu Z.; Li Y.; Liu H.; Zhang L.; Dong Y.; Li X. Straightforward Synthesis of Alkyl Fluorides via Visible-Light-Induced Hydromono- and Difluoroalkylations of Alkenes with α-Fluoro Carboxylic Acids. J. Org. Chem. 2022, 87, 9232–9241..
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531.
Wang J.; Luo Z.; Wu Y.; Tang Y.; Yang X.; Tsui G. C. Copper-Catalyzed Visible-Light-Induced Allylic Difluoromethylation of Unactivated Alkenes Using Difluoroacetic Acid. Org. Lett. 2023, 25, 1045–1049..
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532.
Gui Q.-W.; Teng F.; Yang H.; Xun C.; Huang W.-J.; Lu Z.-Q.; Zhu M.-X.; Ouyang W.-T.; He W.-M. Visible-Light Photosynthesis of CHF2/CClF2/CBrF2-Substituted Ring-fused Quinazolinones in Dimethyl Carbonate. Chem. - Asian J. 2022, 17, e202101139.
Not in our library10.1002/asia.202101139
533.
Gui Q.-W.; Teng F.; Li Z.-C.; Xiong Z.-Y.; Jin X.-F.; Lin Y.-W.; Cao Z.; He W.-M. Visible-Light-Initiated Tandem Synthesis of Difluoromethylated Oxindoles in 2-MeTHF under Additive-, Metal Catalyst-, External Photosensitizer-Free and Mild Conditions. Chin. Chem. Lett. 2021, 32, 1907–1910..
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534.
Sakamoto R.; Tomomi Y.; Takada H.; Maruoka K. A Synthetic Route to Sodium α-Aminoalkanesulfinates and Their Application in the Generation of α-Aminoalkyl Radicals for Radical Addition Reactions. Org. Lett. 2018, 20, 2080–2083..
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535.
Xu X.; Liu F. Transition-Metal-Free Radical tri-/Difluoromethylation of N,N-Dialkylhydrazones with Sodium Sulfinates. Org. Chem. Front. 2017, 4, 2306–2310..
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536.
Wang L.; Zhao J.; Sun Y.; Zhang H.-Y.; Zhang Y. A Catalyst-Free Minisci-Type Reaction: the C-H Alkylation of Quinoxalinones with Sodium Alkylsulfinates and Phenyliodine(III) Dicarboxylates. Eur. J. Org. Chem. 2019, 2019, 6935–6944..
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537.
Wu Z.; He Y.; Ma C.; Zhou X.; Liu X.; Li Y.; Hu T.; Wen P.; Huang G. Oxidative Remote C-H Trifluoromethylation of Quinolineamides on the C5 Position with Iodobenzene Diacetate as the Oxidizing Agent. Asian J. Org. Chem. 2016, 5, 724–728..
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538.
Li X.; Cheng Z.; Liu J.; Zhang Z.; Song S.; Jiao N. Selective Desaturation of Amides: a Direct Approach to Enamides. Chem. Sci. 2022, 13, 9056–9061..
Not in our library10.1039/d2sc02210a
539.
Yu T.-Y.; Zheng Z.-J.; Dang T.-T.; Zhang F.-X.; Wei H. Synthesis of Acyl Azides from 1,3-Diketones via Oxidative Cleavage of Two C-C Bonds. J. Org. Chem. 2018, 83, 10589–10594..
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540.
Matsui D.; Tanimori S. A Quick and Easy Access to a Series of Thiocyanated Enaminones and 2-Iminothiazolones Using PIDA under Mild Conditions. J. Heterocycl. Chem. 2022, 59, 1591–1603..
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541.
Yang Z.; Hu L.; Cao T.; An L.; Li L.; Yang T.; Zhou C. PIDA-Mediated α-C-H Functionalization of Enaminones: the Synthesis of Thiocyano Enaminones and Chromones in Water. New J. Chem. 2019, 43, 16441–16444..
Not in our library10.1039/c9nj04580e
542.
Yuan L.; Liu J.; Huang K.; Wang S.; Jin Y.; Lin J. Cascade Reaction of Tertiary Enaminones, KSCN and Anilines: Temperature-Controlled Synthesis of 2-Aminothiazoles and 2-Iminothiazoline. J. Org. Chem. 2022, 87, 9171–9183..
Not in our library10.1021/acs.joc.2c00918
543.
He C.; Bai Z.; Hu J.; Wang B.; Xie H.; Yu L.; Ding H. A Divergent [5 + 2] Cascade Approach to Bicyclo[3.2.1]octanes: Facile Synthesis of Ent-Kaurene and Cedrene-Type Skeletons. Chem. Commun. 2017, 53, 8435–8438..
Not in our library10.1039/c7cc04292b
544.
Mullapudi V.; Bhogade R. B.; Deshpande M. V.; Ramana C. V. Phenol Oxidative Dearomatization of Modified Nucleoside Templates: A Simple Access to the C7-Spiroannulated Octosyl Acid Framework. Synthesis 2017, 49, 4221–4228..
Not in our library10.1055/s-0036-1588543
545.
Zhao G.-H.; Li B.-Q.; Wang S.-S.; Liu M.; Chen Y.; Wang B. PIFA-Mediated Dearomatizative Spirocyclization of Phenolic Biarylic Ketones via Oxidation and C-C Bond Cleavage. J. Org. Chem. 2020, 85, 9367–9374..
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546.
Scheiber N.; Blaser G.; Pferschy-Wenzig E.-M.; Kaiser M.; Maeser P.; Presser A. Efficient Oxidative Dearomatisations of Substituted Phenols Using Hypervalent Iodine (III) Reagents and Antiprotozoal Evaluation of the Resulting Cyclohexadienones against T. b. rhodesiense and P. falciparum Strain NF54. Molecules 2022, 27, 6559.
Not in our library10.3390/molecules27196559
547.
Depken C.; Kraetzschmar F.; Breder A. Iodine(III)-Mediated Oxidative Intramolecular Arene-Alkene Coupling Exemplified in the Synthesis of Phenanthrenes. Org. Chem. Front. 2016, 3, 314–318..
Not in our library10.1039/c5qo00361j
548.
Hu B.; Cao Y.; Zhang B.; Zhang-Negrerie D.; Du Y. Formation of Phenyliodonio-Substituted Spirofurooxindole Trifluoroacetates from N-Substituted 3-Oxopentanediamides via Phenyliodine Bis(trifluoroacetate)-Mediated Oxidative Cascade Reactions. Adv. Synth. Catal. 2017, 359, 2542–2548..
Not in our library10.1002/adsc.201700075
549.
Peng C.; Liu W.; Ning S.; Ge G.; Zhao Z. K. Oxidative Coupling of â-O-4’ Dilignol Models Leading to Polycyclic Products with Rare Interlignol Linkages. Asian J. Org. Chem. 2017, 6, 1745–1748..
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550.
Zhang B.; Zhang X.; Hu B.; Sun D.; Wang S.; Zhang-Negrerie D.; Du Y. PhI(OCOCF3)2-Mediated Construction of a 2-Spiropseudoindoxyl Skeleton via Cascade Annulation of 2-Sulfonamido-N-phenylpropiolamide Derivatives. Org. Lett. 2017, 19, 902–905..
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551.
Zhou Y.; Zhang X.; Zhang Y.; Ruan L.; Zhang J.; Zhang-Negrerie D.; Du Y. Iodocyclization of N-Arylpropynamides Mediated by Hypervalent Iodine Reagent: Divergent Synthesis of Iodinated Quinolin-2-ones and Spiro[4,5]trienones. Org. Lett. 2017, 19, 150–153..
Not in our library10.1021/acs.orglett.6b03455
552.
Kanyiva K. S.; Tane M.; Shibata T. Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling. J. Org. Chem. 2019, 84, 12773–12783..
Not in our library10.1021/acs.joc.9b01154
553.
Matsumoto M.; Wada K.; Urakawa K.; Ishikawa H. Diaryliodonium Salt-Mediated Intramolecular C-N Bond Formation Using Boron-Masking N-Hydroxyamides. Org. Lett. 2020, 22, 781–785..
Not in our library10.1021/acs.orglett.9b04076
554.
The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones · 2021
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555.
Suzuki Y.; Takehara R.; Miura K.; Ito R.; Suzuki N. Regioselective Synthesis of Trisubstituted Quinoxalines Mediated by Hypervalent Iodine Reagents. J. Org. Chem. 2021, 86, 16892–16900..
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Bera S. K.; Mal P. Regiodivergent C-N Coupling of Quinazolinones Controlled by the Dipole Moments of Tautomers. Org. Lett. 2022, 24, 3144–3148..
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Arepally S.; Babu V. N.; Bakthadoss M.; Sharada D. S. A Direct Cycloaminative Approach to Imidazole Derivatives via Dual C-H Functionalization. Org. Lett. 2017, 19, 5014–5017..
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Morimoto K.; Koseki D.; Dohi T.; Kita Y. Oxidative Biaryl Coupling of N-Aryl Anilines by Using a Hypervalent Iodine(III) Reagent. Synlett 2017, 28, 2941–2945..
Not in our library10.1055/s-0036-1590875
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Ono T.; Koga D.; Yoza K.; Hisaeda Y. The First Synthesis of Meso-Dicycloalkylporphycenes: Ring Strain Effects on Structural And Optical Properties of Isomeric Porphyrins. Chem. Commun. 2017, 53, 12258–12261..
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Ono T.; Koga D.; Hisaeda Y. Facile Synthesis of 9,10,19,20-Tetraalkylporphycenes. Chem. Lett. 2017, 46, 260–262..
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Zhao F.; Sun T.; Sun H.; Xi G.; Sun K. Hypervalent Iodine Mediated Oxidative Radical Amination of Heteroarenes under Metal-Free Conditions. Tetrahedron Lett. 2017, 58, 3132–3135..
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Shen J.; Xu J.; Huang L.; Zhu Q.; Zhang P. Hypervalent Iodine(III)-Promoted Rapid Cascade Reaction of Quinoxalinones with Unactivated Alkenes and TMSN3. Adv. Synth. Catal. 2020, 362, 230–241..
Not in our library10.1002/adsc.201901314
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Chen Q.; Peng C.; Liu W.; Ning S.; Hu G.; Zhao Z. K.; Xie H. Oxidative Coupling of Kraft Lignin Mediated with Hypervalent Iodine Reagent (III) for Enhanced Removal of Dye in Water. Ind. Crops Prod. 2022, 175, 114234.
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Bhattacharjee S.; Laru S.; Hajra A. Hypervalent Iodine(III)-Mediated Oxidative Dearomatization of 2H-Indazoles towards Indazolyl Indazolones. Org. Biomol. Chem. 2022, 20, 8893–8897..
Not in our library10.1039/d2ob01776h
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Tellitu I.; Domínguez E. The Application of [Bis(trifluoroacetoxy)iodo]benzene (PIFA) in the Synthesis of Nitrogen-Containing Heterocycles. Synlett 2012, 23, 2165–2175..
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566.
Tellitu I.; Dominguez E. Recent Applications of the PIFA-Assisted Intramolecular Olefin Amidation Reaction: an Advantageous Approach to the Synthesis of Nitrogen-Containing Heterocycles. Trends Heterocycl. Chem. 2012, 15, 23–32..
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Deprez N. R.; Sanford M. S. Reactions of Hypervalent Iodine Reagents with Palladium: Mechanisms and Applications in Organic Synthesis. Inorg. Chem. 2007, 46, 1924–1935..
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Tian B.; Chen P.; Liu G. Palladium-Catalyzed Intermolecular Carbonylation-Based Difunctionalization of Alkenes. Synlett 2022, 33, 927–938..
Not in our library10.1055/s-0040-1719898
569.
Fan X.-M.; Guo Y.; Li Y.-D.; Yu K.-K.; Liu H.-W.; Liao D.-H.; Ji Y.-F. Pd-Catalyzed Late-Stage Monoacetoxylation and Monoiodination of 4-Alkyl-1,5-diaryl-1H-pyrazole-3-carboxylates via Direct Csp2-H Bond Activation. Asian J. Org. Chem. 2016, 5, 499–505..
Not in our library10.1002/ajoc.201600028
570.
Geng C.; Jiang M.; Feng L.; Jiao P. Palladium Catalyzed C-H bond Acetoxylation: Isoxazolinyl as a Directing Group. RSC Adv. 2016, 6, 56971–56976..
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He G.; Lu G.; Guo Z.; Liu P.; Chen G. Benzazetidine Synthesis via Palladium-catalysed Intramolecular C-H Amination. Nat. Chem. 2016, 8, 1131–1136..
Not in our library10.1038/nchem.2585
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Irastorza A.; Aizpurua J. M.; Correa A. Triazole-Directed Pd-Catalyzed C(sp2)-H Oxygenation of Arenes and Alkenes. Org. Lett. 2016, 18, 1080–1083..
Not in our library10.1021/acs.orglett.6b00195
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Huang Z.; Wang C.; Dong G. A Hydrazone-Based exo-Directing-Group Strategy for β C-H Oxidation of Aliphatic Amines. Angew. Chem., Int. Ed. 2016, 55, 5299–5303..
Not in our library10.1002/anie.201600912
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Li M.; Yu F.; Qi X.; Chen P.; Liu G. Cooperative Strategy for the Highly Selective Intermolecular Oxycarbonylation Reaction of Alkenes using Palladium Catalyst. Angew. Chem., Int. Ed. 2016, 55, 13843–13848..
Not in our library10.1002/anie.201607248
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Jiang T.; Quan X.; Zhu C.; Andersson P. G.; Baeckvall J.-E. Palladium-Catalyzed Oxidative Synthesis of α-Acetoxylated Enones from Alkynes. Angew. Chem., Int. Ed. 2016, 55, 5824–5828..
Not in our library10.1002/anie.201600696
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Li S.; Zhu W.; Gao F.; Li C.; Wang J.; Liu H. Palladium-Catalyzed Ortho-Alkoxylation of N-Benzoyl α-Amino Acid Derivatives at Room Temperature. J. Org. Chem. 2017, 82, 126–134..
Not in our library10.1021/acs.joc.6b02257
577.
Chen K.; Wang D.; Li Z.-W.; Liu Z.; Pan F.; Zhang Y.-F.; Shi Z.-J. Palladium Catalyzed C(sp3)-H Acetoxylation of Aliphatic Primary Amines to γ-Amino Alcohol Derivatives. Org. Chem. Front. 2017, 4, 2097–2101..
Not in our library10.1039/c7qo00432j
578.
Borelli T.; Brenna S.; Broggini G.; Oble J.; Poli G. (Diacyloxyiodo)benzenes-Driven Palladium-Catalyzed Cyclizations of Unsaturated N-Sulfonylamides: Opportunities of Path Selection. Adv. Synth. Catal. 2017, 359, 623–628..
Not in our library10.1002/adsc.201600813
579.
Zhu R.-Y.; Liu L.-Y.; Yu J.-Q. Highly Versatile β-C(sp3)-H Iodination of Ketones Using a Practical Auxiliary. J. Am. Chem. Soc. 2017, 139, 12394–12397..
Not in our library10.1021/jacs.7b06851
580.
Smalley A. P.; Cuthbertson J. D.; Gaunt M. J. Palladium-Catalyzed Enantioselective C-H Activation of Aliphatic Amines Using Chiral Anionic BINOL-Phosphoric Acid Ligands. J. Am. Chem. Soc. 2017, 139, 1412–1415..
Not in our library10.1021/jacs.6b12234
581.
Qiao W.-L.; Shao L.-Y.; Hu Y.-H.; Xing L.-H.; Deng K.-Z.; Liu H.-W.; Liao D.-H.; Ji Y.-F. Palladium-Catalyzed Csp3-H Bond mono-Aroyloxylation of O-Alkyl Substituted 2,4,6-Trimethoxybenzaldoxime Ethers. Synlett 2018, 29, 1249–1255..
Not in our library10.1055/s-0036-1609346
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Qi X.; Chen C.; Hou C.; Fu L.; Chen P.; Liu G. Enantioselective Pd(II)-Catalyzed Intramolecular Oxidative 6-endo Aminoacetoxylation of Unactivated Alkenes. J. Am. Chem. Soc. 2018, 140, 7415–7419..
Not in our library10.1021/jacs.8b03767
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Zheng Y.; Song W.; Zhu Y.; Wei B.; Xuan L. Pd-Catalyzed Acetoxylation of γ-C(sp3)-H Bonds of Amines Directed by a Removable Bts-Protecting Group. J. Org. Chem. 2018, 83, 2448–2454..
Not in our library10.1021/acs.joc.7b02995
584.
Xu T.; Wang D.; Tong X. Pd(II)-Catalyzed Intramolecular Acetoxylative (3 + 2) Annulation of Propargylic Alcohol and Alkene: Polycyclic Oxa-heterocycle Synthesis and Mechanistic Insight. Org. Lett. 2019, 21, 5368–5372..
Not in our library10.1021/acs.orglett.9b02096
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Ghosh K. K.; Uttry A.; Koldemir A.; Ong M.; van Gemmeren M. Direct β-C(sp3)-H Acetoxylation of Aliphatic Carboxylic Acids. Org. Lett. 2019, 21, 7154–7157..
Not in our library10.1021/acs.orglett.9b02741
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Buettner C. S.; Willcox D.; Chappell B. G. N.; Gaunt M. J. Mechanistic Investigation into the C(sp3)-H Acetoxylation of Morpholinones. Chem. Sci. 2019, 10, 83–89..
Not in our library10.1039/c8sc03434f
587.
Sato T.; Nogi K.; Yorimitsu H. Palladium-Catalyzed peri-Selective C-H Fluoroalkoxylation of Aryl Sulfoxides. ChemCatChem. 2020, 12, 3467–3471..
Not in our library10.1002/cctc.202000485
588.
Giofre S.; Molteni L.; Nava D.; Lo Presti L.; Beccalli E. M. Enantio- and Regioselective Palladium(II)-Catalyzed Dioxygenation of (Aza-)Alkenols. Angew. Chem., Int. Ed. 2021, 60, 21723–21727..
Not in our library10.1002/anie.202109312
589.
Sarkar A.; Saha M.; Das A. R.; Banerjee A.; Majumder R.; Bandyopadhyay D. Hypervalent Iodine Mediated Pd(II)-catalyzed ortho-C(sp2-H) Functionalization of Azoles Deciphering Hantzsch Ester and Malononitrile as the Functional Group Surrogates. ChemistrySelect 2022, 7, e202203959.
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Mao S.; Tang L.; Wu C.; Tu X.; Gao Q.; Deng G. Ag(I)-Catalyzed Tandem Reaction of Conjugated Ene-yne-ketones in the Presence of PhI(OAc)2 and Triethylamine: Synthesis of 2-Alkenylfurans. Org. Lett. 2019, 21, 2416–2420..
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Chen H.; Wang J.; Hu Z.; Xu S.; Shi M.; Zhang J. Catalytic Domino Amination and Oxidative Coupling of Gold Acetylides and Isolation of Key Vinylene Digold Intermediates as a New Class of Ditopic N-Heterocyclic Carbene Complexes. Chem. Commun. 2017, 53, 10835–10838..
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Xie L.-Y.; Jiang L.-L.; Tan J.-X.; Wang Y.; Xu X.-Q.; Zhang B.; Cao Z.; He W.-M. Visible-Light-Initiated Decarboxylative Alkylation of Quinoxalin-2(1H)-ones with Phenyliodine(III) Dicarboxylates in Recyclable Ruthenium(II) Catalytic System. ACS Sustainable Chem. Eng. 2019, 7, 14153–14160..
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Zhang X.-Y.; Ning C.; Long Y.-J.; Wei Y.; Shi M. Visible-Light-Mediated Decarboxylative Tandem Carbocyclization of Acrylamide-Attached Alkylidenecyclopropanes: Access to Polycyclic Benzazepine Derivatives. Org. Lett. 2020, 22, 5212–5216..
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Ghosh S. K.; Hu M.; Comito R. J. One-Pot Synthesis of Primary and Secondary Aliphatic Amines via Mild and Selective sp3 C-H Imination. Chem. - Eur. J. 2021, 27, 17601–17608..
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Cardenal A. D.; Maity A.; Gao W.-Y.; Ashirov R.; Hyun S.-M.; Powers D. C. Iodosylbenzene Coordination Chemistry Relevant to Metal-Organic Framework Catalysis. Inorg. Chem. 2019, 58, 10543–10553..
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Yudasaka M.; Maruyama T.; Yamaguchi E.; Tada N.; Itoh A. Synthesis, Characterization, and Reaction of a Both Inter- and Intramolecularly Coordinated Pseudocyclic Iodosylbenzene-Trifluoroacetic Acid Complexes. Eur. J. Org. Chem. 2018, 2018, 550–556..
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Au-Yeung K.-C.; So Y.-M.; Wang G.-C.; Sung H. H. Y.; Williams I. D.; Leung W.-H. Iodosylbenzene and Iodylbenzene Adducts of Cerium(IV) Complexes Bearing Chelating Oxygen Ligands. Dalton Trans. 2016, 45, 5434–5438..
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de Ruiter G.; Carsch K. M.; Gul S.; Chatterjee R.; Thompson N. B.; Takase M. K.; Yano J.; Agapie T. Accelerated Oxygen Atom Transfer and C-H Bond Oxygenation by Remote Redox Changes in Fe3Mn-Iodosobenzene Adducts. Angew. Chem., Int. Ed. 2017, 56, 4772–4776..
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Jeong D.; Ohta T.; Cho J. Structure and Reactivity of a Mononuclear Nonheme Manganese(III)-Iodosylarene Complex. J. Am. Chem. Soc. 2018, 140, 16037–16041..
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Yang J.; Seo M. S.; Kim K. H.; Lee Y.-M.; Fukuzumi S.; Shearer J.; Nam W. Structure and Unprecedented Reactivity of a Mononuclear Nonheme Cobalt(III) Iodosylbenzene Complex. Angew. Chem., Int. Ed. 2020, 59, 13581–13585..
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Pan Y.; Zhou M.; Wang R.; Song D.; Yiu S.-M.; Xie J.; Lau K.-C.; Lau T.-C.; Liu Y. Structure and Reactivity of a Seven-Coordinate Ruthenium Iodosylbenzene Complex. Inorg. Chem. 2023, 62, 7772–7778..
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Hill E. A.; Kelty M. L.; Filatov A. S.; Anderson J. S. Isolable iodosylarene and iodoxyarene adducts of Co and their O-atom transfer and C-H activation reactivity. Chem. Sci. 2018, 9, 4493–4499..
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Miyamoto K.; Watanabe Y.; Takagi T.; Okada T.; Toyama T.; Imamura S.; Uchiyama M. CO2-Activated NaClO-5H2O Enabled Smooth Oxygen Transfer to Iodoarene: a Highly Practical Synthesis of Iodosylarene. ARKIVOC 2022, 2021 (vii), 1–11..
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Sarkar S.; Ghosh M. K.; Kalek M. Synthesis of Pummerer’s Ketone and its Analogs by Iodosobenzene-Promoted Oxidative Phenolic Coupling. Tetrahedron Lett. 2020, 61, 152459.
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Zhang H.; Wirth T. Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones. Chem. - Eur. J. 2022, 28, e202200181.
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Li L.; Li X.; Wang W.; He Q.; Fan R. Synthesis of 4-Alkylindoles from 2-Alkynylanilines via Dearomatization- and Aromatization-Triggered Alkyl Migration. Org. Lett. 2021, 23, 2130–2134..
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He J.; Zhang X.; He Q.; Guo H.; Fan R. Synthesis of 15N-Labeled Heterocycles via the Cleavage of C-N Bonds of Anilines and Glycine-15N. Chem. Commun. 2021, 57, 5442–5445..
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Li X.; He Q.; Fan R. Divergent Synthesis of 4-Amino Indoles with Free Amine Groups via Tandem Reaction of 2-Alkynylanilines. Org. Chem. Front. 2022, 9, 4146–4150..
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Li Q.; Zhuang C.; Wang D.; Zhang W.; Jia R.; Sun F.; Zhang Y.; Du Y. Construction of Trisubstituted Chromone Skeletons Carrying Electron-Withdrawing Groups via PhIO-Mediated Dehydrogenation and its Application to the Synthesis of Frutinone A. Beilstein J. Org. Chem. 2019, 15, 2958–2965..
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Li J.; Bauer A.; Di Mauro G.; Maulide N. α-Arylation of Carbonyl Compounds through Oxidative C-C Bond Activation. Angew. Chem., Int. Ed. 2019, 58, 9816–9819..
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Deng R.; Zhan S.; Li C.; Gu Z. Hypervalent-Iodine-Mediated Carbon-Carbon Bond Cleavage and Dearomatization of 9H-Fluoren-9-ols. Angew. Chem., Int. Ed. 2020, 59, 3093–3098..
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Xu Y.-Y.; Gao Z.-H.; Li C.-B.; Ye S. Enantioselective N-Heterocyclic Carbene Catalyzed α-Oxidative Coupling of Enals with Carboxylic Acids Using an Iodine(III) Reagent. Angew. Chem., Int. Ed. 2023, 62, e202218362.
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Matos P. M.; Lewis W.; Moore J. C.; Stockman R. A. Sulfonimidates: Useful Synthetic Intermediates for Sulfoximine Synthesis via C-S Bond Formation. Org. Lett. 2018, 20, 3674–3677..
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Ohura A.; Itoh T.; Ishida H.; Saito A.; Yamamoto K. Three-Component Regioselective Synthesis of Tetrahydrofuro[2,3-d]oxazoles and Their Efficient Conversion to Oxazoles. Asian J. Org. Chem. 2017, 6, 673–676..
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Suzuki S.; Saito A. Single-Step Synthesis of Iodinated Oxazoles from N-Propargyl Amides Mediated by I2/Iodosylbenzene/Trimethylsilyl Trifluoromethanesulfonate Systems. J. Org. Chem. 2017, 82, 11859–11864..
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Han Y.-C.; Zhang Y.-D.; Jia Q.; Cui J.; Zhang C. Hypervalent-Iodine-Mediated Ring-Contraction Monofluorination Affording Monofluorinated Five-Membered Ring-Fused Oxazolines. Org. Lett. 2017, 19, 5300–5303..
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Li C.; Yuan J.; Zhang Q.; Bhujanga Rao C.; Zhang R.; Zhao Y.; Deng B.; Dong D. Oxidative Cyclization of β-Aminoacrylamides Mediated by PhIO: Chemoselective Synthesis of Isoxazoles and 2H-Azirines. J. Org. Chem. 2018, 83, 14999–15008..
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Garia A.; Chauhan P.; Halder R.; Jain N. Quinoline-Fused Lactones via Tandem Oxidation Cyclization: Metal-Free sp3 C-H Functionalization. J. Org. Chem. 2021, 86, 538–546..
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Garia A.; Grover J.; Jain N. Metal-Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho-Carbonyl Anilines. Eur. J. Org. Chem. 2021, 2021, 4125–4131..
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Ishida H.; Homma S.; Kasuga R.; Yamamoto K.; Itoh T. Synthesis of Tetrahydrofuro[2,3-d]-oxazoles and Oxazoles by Hypervalent Iodine (III)-Promoted [2 + 2+1] Annulation. Chem. Pharm. Bull. 2022, 70, 192–194..
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Mukherjee P.; Das A. R. Spirocyclopropanes from Intramolecular Cyclopropanation of Pyranopyrazoles and Pyranopyrimidine-diones and Lewis Acid Mediated [3 + 2] Cycloadditions of Spirocyclopropylpyrazolones. J. Org. Chem. 2017, 82, 2794–2802..
Not in our library10.1021/acs.joc.7b00089
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Bhujanga Rao C.; Yuan J.; Zhang Q.; Zhang R.; Zhang N.; Fang J.; Dong D. Iodosobenzene-Mediated α-Acyloxylation of 1,3-Dicarbonyl Compounds with Carboxylic Acids and Insight into the Reaction Mechanism. J. Org. Chem. 2018, 83, 2904–2911..
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Ye X.; Zhang R.; Wang Y.; Li J.; Dong D. PhIO-Mediated Cascade Reactions of Activated Acetylamides and Cyclic Amidines: Access to Polysubstituted Imidazolidin-2-ones. Asian J. Org. Chem. 2023, 12, e202300346.
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Li S.; Sun Y.; Li X.; Smaga O.; Koniarz S.; Pawlicki M.; Chmielewski P. J. Oxidative Insertion of Amines into Conjugated Macrocycles: Transformation of Antiaromatic Norcorrole into Aromatic Azacorrole. Chem. Commun. 2023, 59, 3739–3742..
Not in our library10.1039/d2cc06648c
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Zhen X.; Wan X.; Zhang W.; Li Q.; Zhang-Negrerie D.; Du Y. Synthesis of Spirooxindoles from N-Arylamide Derivatives via Oxidative C(sp2)-C(sp3) Bond Formation Mediated by PhI(OMe)2 Generated in Situ. Org. Lett. 2019, 21, 890–894..
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Zhang J.; Jalil A.; He J.; Yu Z.; Cheng Y.; Li G.; Du Y.; Zhao K. Lactonization with Concomitant 1,2-Aryl Migration and Alkoxylation Mediated by Dialkoxyphenyl Iodides Generated In Situ. Chem. Commun. 2021, 57, 7426–7429..
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Liang Z.-P.; Yi W.; Wang P.-F.; Liu G.-Q.; Ling Y. Iodosobenzene-Mediated Three-Component Selenofunctionalization of Olefins. J. Org. Chem. 2021, 86, 5292–5304..
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Wang P.-F.; Yi W.; Ling Y.; Ming L.; Liu G.-Q.; Zhao Y. Preparation of Selenofunctionalized Heterocycles via Iodosobenzene-Mediated Intramolecular Selenocyclizations of Olefins with Diselenides. Chin. Chem. Lett. 2021, 32, 2587–2591..
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Satkar Y.; Yera-Ledesma L. F.; Mali N.; Patil D.; Navarro-Santos P.; Segura-Quezada L. A.; Ramirez-Morales P. I.; Solorio-Alvarado C. R. Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols. J. Org. Chem. 2019, 84, 4149–4164..
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Yahuaca-Juarez B.; Gonzalez G.; Ramirez-Morales M. A.; Alba-Betancourt C.; Deveze-Alvarez M. A.; Mendoza-Macias C. L.; Ortiz-Alvarado R.; Juarez-Ornelas K. A.; Solorio-Alvarado C. R.; Maruoka K. Iodine(III)-Catalyzed Benzylic Oxidation by using the (PhIO)n/Al(NO3)3 System. Synth. Commun. 2020, 50, 539–548..
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Juarez-Ornelas K. A.; Jimenez-Halla J. O. C.; Kato T.; Solorio-Alvarado C. R.; Maruoka K. Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Bronsted Acidic NO2+ Generation. Org. Lett. 2019, 21, 1315–1319..
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677.
Segura-Quezada A.; Satkar Y.; Patil D.; Mali N.; Wrobel K.; Gonzalez G.; Zarraga R.; Ortiz-Alvarado R.; Solorio-Alvarado C. R. Iodine(III)/AlX3-Mediated Electrophilic Chlorination and Bromination of Arenes. Dual rRle of AlX3 (X = Cl, Br) for (PhIO)n Depolymerization and as the Halogen Source. Tetrahedron Lett. 2019, 60, 1551–1555..
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Patil D. B.; Gamez-Montano R.; Ordonez M.; Solis-Santos M.; Jimenez-Halla J. O. C.; Solorio-Alvarado C. R. Iodine(III)-Mediated Electrophilic Chlorination and Catalytic Nitration of N-Tosyl Anilines. Eur. J. Org. Chem. 2022, 2022, e202201295.
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Li Z.; Zhang G. a.; Song Y.; Li M.; Li Z.; Ding W.; Wu J. Copper-Catalyzed Enantioselective Decarboxylative Cyanation of Benzylic Acids Promoted by Hypervalent Iodine(III) Reagents. Org. Lett. 2023, 25, 3023–3028..
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Zhang Y.; Zhao X.; Zhuang C.; Wang S.; Zhang-Negrerie D.; Du Y. PhIO/Et3N·3HF-Mediated Formation of Fluorinated 2H-Azirines via Domino Fluorination/Azirination Reaction of Enamines. Adv. Synth. Catal. 2018, 360, 2107–2112..
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Kitamura T.; Mizuno S.; Muta K.; Oyamada J. Synthesis of β-Fluorovinyliodonium Salts by the Reaction of Alkynes with Hypervalent Iodine/HF Reagents. J. Org. Chem. 2018, 83, 2773–2778..
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Feng S.-X.; Yang S.; Tu F.-H.; Lin P.-P.; Huang L.-L.; Wang H.; Huang Z.-S.; Li Q. Iodine(III)-Mediated Fluorination/Semipinacol Rearrangement Cascade of 2-Alkylidenecyclobutanol Derivatives: Access to β-Monofluorinated Cyclopropanecarbaldehydes. J. Org. Chem. 2021, 86, 6800–6812..
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Li W.; Kitamura T.; Zhou Y.; Butler G.; Han J.; Soloshonok V. A. Electrophilic Fluorination Using PhIO/HF·THF Reagent. J. Fluorine Chem. 2020, 240, 109670.
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Chen N.; Deng T.-T.; Li J.-Q.; Cui X.-Y.; Sun W.-W.; Wu B. Hypervalent Iodine(III)-Mediated Umpolung Dialkoxylation of N-Substituted Indoles. J. Org. Chem. 2022, 87, 12759–12771..
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Maity S.; Szpilman A. M. 2-Fluoroenones via an Umpolung Morita-Baylis-Hillman Reaction of Enones. Org. Lett. 2023, 25, 1218–1222..
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Karmalkar D. G.; Li X.-X.; Seo M. S.; Sankaralingam M.; Ohta T.; Sarangi R.; Hong S.; Nam W. A Manganese(V)-Oxo Tetraamido Macrocyclic Ligand (TAML) Cation Radical Complex: Synthesis, Characterization, and Reactivity Studies. Chem. - Eur. J. 2018, 24, 17927–17931..
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687.
Liu W.; Huang X.; Placzek M. S.; Krska S. W.; McQuade P.; Hooker J. M.; Groves J. T. Site-selective 18F Fluorination of Unactivated C-H Bonds Mediated by a Manganese Porphyrin. Chem. Sci. 2018, 9, 1168–1172..
Not in our library10.1039/c7sc04545j
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Ge Y.; Su X.; Li G.; Yang Y.-F.; She Y. Oxidative Functionalization of Naphthalene Derivatives Catalyzed by Mn(III)-Porphyrins. Tetrahedron Lett. 2023, 123, 154535.
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Jeong D.; Kim H.; Cho J. Oxidation of Aldehydes into Carboxylic Acids by a Mononuclear Manganese(III) Iodosylbenzene Complex through Electrophilic C-H Bond Activation. J. Am. Chem. Soc. 2023, 145, 888–897..
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Burg F.; Buchelt C.; Kreienborg N. M.; Merten C.; Bach T. Enantioselective Synthesis of Diaryl Sulfoxides Enabled by Molecular Recognition. Org. Lett. 2021, 23, 1829–1834..
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691.
Sun S.; Ma Y.; Liu Z.; Liu L. Oxidative Kinetic Resolution of Cyclic Benzylic Ethers. Angew. Chem., Int. Ed. 2021, 60, 176–180..
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Cao M.; Wang H.; Ma Y.; Tung C.-H.; Liu L. Site- and Enantioselective Manganese-Catalyzed Benzylic C-H Azidation of Indolines. J. Am. Chem. Soc. 2022, 144, 15383–15390..
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Liu Z.-J.; Lu X.; Wang G.; Li L.; Jiang W.-T.; Wang Y.-D.; Xiao B.; Fu Y. Directing Group in Decarboxylative Cross-Coupling: Copper-Catalyzed Site-Selective C-N Bond Formation from Nonactivated Aliphatic Carboxylic Acids. J. Am. Chem. Soc. 2016, 138, 9714–9719..
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Wang Q.; Chen X.; Li G.; Chen Q.; Yang Y.-F.; She Y.-B. Computational Exploration of Chiral Iron Porphyrin-Catalyzed Asymmetric Hydroxylation of Ethylbenzene Where Stereoselectivity Arises from π-π Stacking Interaction. J. Org. Chem. 2019, 84, 13755–13763..
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695.
Doiuchi D.; Nakamura T.; Hayashi H.; Uchida T. Non-Heme-Type Ruthenium Catalyzed Chemo- and Site-Selective C-H Oxidation. Chem. - Asian J. 2020, 15, 762–765..
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696.
He Q.; Pu M.-P.; Jiang Z.; Wang H.; Feng X.; Liu X. Asymmetric Epoxidation of Alkenes Catalyzed by a Cobalt Complex. J. Am. Chem. Soc. 2023, 145, 15611–15618..
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Lucchetti N.; Tkacheva A.; Fantasia S.; Muniz K. Radical C-H-Amination of Heteroarenes using Dual Initiation by Visible Light and Iodine. Adv. Synth. Catal. 2018, 360, 3889–3893..
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Gunsalus N.; Koppaka A.; Chen S.-S.; Park S. H.; Hashiguchi B. G.; Ess D. H.; Periana R. A. Reactivity and Mechanisms of Methane, Ethane, and Benzene C-H Amination with an Iodine(III) Bistriflimide Complex. Organometallics 2023, 42, 1505–1512..
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Bosnidou A. E.; Millan A.; Ceballos J.; Martinez C.; Muniz K. Iodine(III)-Mediated Selective Intermolecular C-H Amination for the Chemical Diversification of Tryptamines. J. Org. Chem. 2016, 81, 6496–6504..
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700.
Roeben C.; Souto J. A.; Gonzalez Y.; Lishchynskyi A.; Muniz K. Enantioselective Metal-Free Diamination of Styrenes. Angew. Chem., Int. Ed. 2011, 50, 9478–9482..
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701.
Nangunuri B. G.; Shirke R. P.; Kim M.-h. Metal-Free Synthesis of Dihydrofuran Derivatives as Anti-Vicinal Amino Alcohol Isosteres. Org. Biomol. Chem. 2023, 21, 960–965..
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702.
Moriyama K.; Hamada T.; Ishida K.; Togo H. 1,3-Iodo-Amination of 2-Methylindoles via Csp2-Csp3 Dual Functionalization with Iodine Reagent. Chem. Commun. 2018, 54, 4258–4261..
Not in our library10.1039/c8cc00352a
703.
Xiang D.; Li H.; Zhang L.; Zhang Y.; Zhang Q.; Li D. Divergent Reactions between Alkynes and Dibenzenesulfonimide: Selective Synthesis of Ynamides and Enamides under Metal-Free Conditions. Asian J. Org. Chem. 2019, 8, 537–541..
Not in our library10.1002/ajoc.201900110
704.
Jeon H.; Kim D.; Lee J. H.; Song J.; Lee W. S.; Kang D. W.; Kang S.; Lee S. B.; Choi S.; Hong K. B. Hypervalent Iodine-Mediated Alkene Functionalization: Oxazoline and Thiazoline Synthesis via Inter-/Intramolecular Aminohydroxylation and Thioamination. Adv. Synth. Catal. 2018, 360, 779–783..
Not in our library10.1002/adsc.201701087
705.
Baeten M.; Maes B. U. W. Guanidine Synthesis: Use of Amidines as Guanylating Agents. Adv. Synth. Catal. 2016, 358, 826–833..
Not in our library10.1002/adsc.201501146
706.
Desnoyer A. N.; Nicolay A.; Ziegler M. S.; Lakshmi K. V.; Cundari T. R.; Tilley T. D. A Dicopper Nitrenoid by Oxidation of a CuICuI Core: Synthesis, Electronic Structure, and Reactivity. J. Am. Chem. Soc. 2021, 143, 7135–7143..
Not in our library10.1021/jacs.1c02235
707.
Hong S.; Sutherlin K. D.; Vardhaman A. K.; Yan J. J.; Park S.; Lee Y.-M.; Jang S.; Lu X.; Ohta T.; Ogura T.; Solomon E. I.; Nam W. A Mononuclear Nonheme Iron(V)-Imido Complex. J. Am. Chem. Soc. 2017, 139, 8800–8803..
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708.
Goure E.; Senthilnathan D.; Coin G.; Albrieux F.; Avenier F.; Dubourdeaux P.; Lebrun C.; Maldivi P.; Latour J.-M. Redox Self-Adaptation of a Nitrene Transfer Catalyst to the Substrate Needs. Angew. Chem., Int. Ed. 2017, 56, 4305–4309..
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709.
Anderson C. M.; Aboelenen A. M.; Jensen M. P. Competitive Intramolecular Amination as a Clock for Iron-Catalyzed Nitrene Transfer. Inorg. Chem. 2019, 58, 1107–1119..
Not in our library10.1021/acs.inorgchem.8b02284
710.
Elkoush T.; Mak C. L.; Paley D. W.; Campbell M. G. Silver(II) and Silver(III) Intermediates in Alkene Aziridination with a Dinuclear Silver(I) Nitrene Transfer Catalyst. ACS Catal. 2020, 10, 4820–4826..
Not in our library10.1021/acscatal.0c00065
711.
Yang F.; Ruan J.; Zavalij P. Y.; Vedernikov A. N. An Electron-Poor Dioxa-[2.1.1]-(2,6)-pyridinophane Ligand and Its Application in Cu-Catalyzed Olefin Aziridination. Inorg. Chem. 2019, 58, 15562–15572..
Not in our library10.1021/acs.inorgchem.9b02618
712.
van Leest N. P.; Tepaske M. A.; Venderbosch B.; Oudsen J.-P. H.; Tromp M.; van der Vlugt J. I.; de Bruin B. Electronically Asynchronous Transition States for C-N Bond Formation by Electrophilic [CoIII(TAML)]-Nitrene Radical Complexes Involving Substrate-to-Ligand Single-Electron Transfer and a Cobalt-Centered Spin Shuttle. ACS Catal. 2020, 10, 7449–7463..
Not in our library10.1021/acscatal.0c01343
713.
Rodriguez M. R.; Besora M.; Molina F.; Maseras F.; Diaz-Requejo M. M.; Perez P. J. Intermolecular Allene Functionalization by Silver-Nitrene Catalysis. J. Am. Chem. Soc. 2020, 142, 13062–13071..
Not in our library10.1021/jacs.0c04395
714.
Kobayashi T.; Kumagai N. Oxa-TriQuinoline: A New Entry to Aza-Oxa-Crown Architectures. Angew. Chem., Int. Ed. 2023, 62, e202307896.
Not in our library10.1002/anie.202307896
715.
Makino K.; Kumagai Y.; Yoshino T.; Kojima M.; Matsunaga S. Catalytic Enantioselective Amination of Enol Silyl Ethers Using a Chiral Paddle-Wheel Diruthenium Complex. Org. Lett. 2023, 25, 3234–3238..
Not in our library10.1021/acs.orglett.3c00940
716.
Ju M.; Huang M.; Vine L. E.; Dehghany M.; Roberts J. M.; Schomaker J. M. Tunable Catalyst-Controlled Syntheses of β- and γ-Amino Alcohols Enabled by Silver-Catalysed Nitrene Transfer. Nat. Catal. 2019, 2, 899–908..
Not in our library10.1038/s41929-019-0339-y
717.
Deng T.; Mazumdar W.; Yoshinaga Y.; Patel P. B.; Malo D.; Malo T.; Wink D. J.; Driver T. G. Rh2(II)-Catalyzed Intermolecular N-Aryl Aziridination of Olefins using Nonactivated N-Atom Precursors. J. Am. Chem. Soc. 2021, 143, 19149–19159..
Not in our library10.1021/jacs.1c09229
718.
Fanourakis A.; Williams B. D.; Paterson K. J.; Phipps R. J. Enantioselective Intermolecular C-H Amination Directed by a Chiral Cation. J. Am. Chem. Soc. 2021, 143, 10070–10076..
Not in our library10.1021/jacs.1c05206
719.
Corbin J. R.; Schomaker J. M. Tunable Differentiation of Tertiary C-H Bonds in Intramolecular Transition Metal-Catalyzed Nitrene Transfer Reactions. Chem. Commun. 2017, 53, 4346–4349..
Not in our library10.1039/c7cc01235g
720.
Kono M.; Harada S.; Nemoto T. Chemoselective Intramolecular Formal Insertion Reaction of Rh-Nitrenes into an Amide Bond Over C-H Insertion. Chem. - Eur. J. 2019, 25, 3119–3124..
Not in our library10.1002/chem.201805878
721.
Betz K. N.; Chiappini N. D.; Du Bois J. Intermolecular sp3-C-H Amination for the Synthesis of Saturated Azacycles. Org. Lett. 2020, 22, 1687–1691..
Not in our library10.1021/acs.orglett.9b04096
722.
Hong K.; Zhou S.; Hu W.; Xu X. Rh-Catalyzed Nitrene Alkyne Metathesis/Formal C-N Bond Insertion Cascade: Synthesis of 3-Iminoindolines. Org. Chem. Front. 2020, 7, 1327–1333..
Not in our library10.1039/d0qo00294a
723.
Hodges M. N.; Elardo M. J.; Seo J.; Dohoda A. F.; Michael F. E.; Golder M. R. Upcycling of Polybutadiene Facilitated by Selenium-Mediated Allylic Amination. Angew. Chem., Int. Ed. 2023, 62, e202303115.
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724.
Tokumasu K.; Yazaki R.; Ohshima T. Direct Catalytic Chemoselective α-Amination of Acylpyrazoles: A Concise Route to Unnatural α-Amino Acid Derivatives. J. Am. Chem. Soc. 2016, 138, 2664–2669..
Not in our library10.1021/jacs.5b11773
725.
Wang L.; Agnew D. W.; Yu X.; Figueroa J. S.; Cohen S. M. A Metal-Organic Framework with Exceptional Activity for C-H Bond Amination. Angew. Chem., Int. Ed. 2018, 57, 511–515..
Not in our library10.1002/anie.201709420
726.
Clark J. R.; Feng K.; Sookezian A.; White M. C. Manganese-Catalysed Benzylic C(sp3)-H Amination for Late-Stage Functionalization. Nat. Chem. 2018, 10, 583–591..
Not in our library10.1038/s41557-018-0020-0
727.
Liu B.; Xie P.; Zhao J.; Wang J.; Wang M.; Jiang Y.; Chang J.; Li X. Rhodium-Catalyzed Enantioselective Synthesis of β-Amino Alcohols via Desymmetrization of gem-Dimethyl Groups. Angew. Chem., Int. Ed. 2021, 60, 8396–8400..
Not in our library10.1002/anie.202014080
728.
Coin G.; Dubourdeaux P.; Avenier F.; Patra R.; Castro L.; Lebrun C.; Bayle P.-A.; Pecaut J.; Blondin G.; Maldivi P.; Latour J.-M. Experiments and DFT Computations Combine to Decipher Fe-Catalyzed Amidine Synthesis through Nitrene Transfer and Nitrile Insertion. ACS Catal. 2021, 11, 2253–2266..
Not in our library10.1021/acscatal.0c03791
729.
Rodriguez A. M.; Perez-Ruiz J.; Molina F.; Poveda A.; Perez-Soto R.; Maseras F.; Diaz-Requejo M. M.; Perez P. J. Introducing the Catalytic Amination of Silanes via Nitrene Insertion. J. Am. Chem. Soc. 2022, 144, 10608–10614..
Not in our library10.1021/jacs.2c03739
730.
Maestre L.; Dorel R.; Pablo O.; Escofet I.; Sameera W. M. C.; Alvarez E.; Maseras F.; Diaz-Requejo M. M.; Echavarren A. M.; Perez P. J. Functional-Group-Tolerant, Silver-Catalyzed N-N Bond Formation by Nitrene Transfer to Amines. J. Am. Chem. Soc. 2017, 139, 2216–2223..
Not in our library10.1021/jacs.6b08219
731.
Annapureddy R. R.; Burg F.; Gramueller J.; Golub T. P.; Merten C.; Huber S. M.; Bach T. Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions. Angew. Chem., Int. Ed. 2021, 60, 7920–7926..
Not in our library10.1002/anie.202016561
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van Leest N. P.; van der Vlugt J. I.; de Bruin B. Catalytic Chemoselective Sulfimidation with an Electrophilic [CoIII(TAML)]–Nitrene Radical Complex**. Chem. - Eur. J. 2021, 27, 371–378..
Not in our library10.1002/chem.202003566
733.
Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides · 2016
No notice
734.
Tota A.; Zenzola M.; Chawner S. J.; John-Campbell S. S.; Carlucci C.; Romanazzi G.; Degennaro L.; Bull J. A.; Luisi R. Synthesis of NH-Sulfoximines from Sulfides by Chemoselective One-Pot N- and O-Transfers. Chem. Commun. 2017, 53, 348–351..
Not in our library10.1039/c6cc08891k
735.
Chaabouni S.; Lohier J.-F.; Barthelemy A.-L.; Glachet T.; Anselmi E.; Dagousset G.; Diter P.; Pegot B.; Magnier E.; Reboul V. One-Pot Synthesis of Aryl- and Alkyl S-Perfluoroalkylated NH-Sulfoximines from Sulfides. Chem. - Eur. J. 2018, 24, 17006–17010..
Not in our library10.1002/chem.201805055
736.
Tota A.; St John-Campbell S.; Briggs E. L.; Estevez G. O.; Afonso M.; Degennaro L.; Luisi R.; Bull J. A. Highly Chemoselective NH- and O-Transfer to Thiols Using Hypervalent Iodine Reagents: Synthesis of Sulfonimidates and Sulfonamides. Org. Lett. 2018, 20, 2599–2602..
Not in our library10.1021/acs.orglett.8b00788
737.
Briggs E. L.; Tota A.; Colella M.; Degennaro L.; Luisi R.; Bull J. A. Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy-amino-λ6-sulfanenitrile Intermediate. Angew. Chem., Int. Ed. 2019, 58, 14303–14310..
Not in our library10.1002/anie.201906001
738.
Tota A.; Colella M.; Carlucci C.; Aramini A.; Clarkson G.; Degennaro L.; Bull J. A.; Luisi R. N-N Bond Formation Using an Iodonitrene as an Umpolung of Ammonia: Straightforward and Chemoselective Synthesis of Hydrazinium Salts. Adv. Synth. Catal. 2021, 363, 194–199..
Not in our library10.1002/adsc.202001047
739.
Hui C.; Brieger L.; Strohmann C.; Antonchick A. P. Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines. J. Am. Chem. Soc. 2021, 143, 18864–18870..
Not in our library10.1021/jacs.1c10175
740.
Verbelen B.; Siemes E.; Ehnbom A.; Raeuber C.; Rissanen K.; Woell D.; Bolm C. From One-Pot NH-Sulfoximidations of Thiophene Derivatives to Dithienylethene-Type Photoswitches. Org. Lett. 2019, 21, 4293–4297..
Not in our library10.1021/acs.orglett.9b01475
741.
Baer R. M.; Langer L.; Nieger M.; Braese S. Bicyclo[1.1.1]pentyl Sulfoximines: Synthesis and Functionalizations. Adv. Synth. Catal. 2020, 362, 1356–1361..
Not in our library10.1002/adsc.201901453
742.
Bull J. A.; Degennaro L.; Luisi R. Straightforward Strategies for the Preparation of NH-Sulfoximines: A Serendipitous Story. Synlett 2017, 28, 2525–2538..
Not in our library10.1055/s-0036-1590874
743.
Lohier J.-F.; Glachet T.; Marzag H.; Gaumont A.-C.; Reboul V. Mechanistic Investigation of the NH-Sulfoximination of Sulfide. Evidence for λ6-Sulfanenitrile Intermediates. Chem. Commun. 2017, 53, 2064–2067..
Not in our library10.1039/c6cc09940h
744.
Combee L. A.; Raya B.; Wang D.; Hilinski M. K. Organocatalytic Nitrenoid Transfer: Metal-Free Selective Intermolecular C(sp3)-H Amination Catalyzed by an Iminium Salt. Chem. Sci. 2018, 9, 935–939..
Not in our library10.1039/c7sc03968a
745.
Johnson S. L.; Hilinski M. K. Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight. J. Org. Chem. 2019, 84, 8589–8595..
Not in our library10.1021/acs.joc.9b01023
746.
Bhattacharjee S.; Hajra A. Imino-λ3-iodane-Triggered Oxidative Ring-Opening of 2H-Indazoles to ortho-N-Acylsulfonamidated Azobenzenes. Org. Lett. 2023, 25, 4183–4187..
Not in our library10.1021/acs.orglett.3c01498
747.
Passia M. T.; Bormann N.; Ward J. S.; Rissanen K.; Bolm C. Synthesis of N-Monosubstituted Sulfondiimines by Metal-free Iminations of Sulfiliminium Salts. Angew. Chem., Int. Ed. 2023, 62, e202305703.
Not in our library10.1002/anie.202305703
748.
Makitalo C. L.; Yoshimura A.; Rohde G. T.; Mironova I. A.; Yusubova R. Y.; Yusubov M. S.; Zhdankin V. V.; Saito A. Imino-λ3-iodane and Catalytic Amount of I2-Mediated Synthesis of N-Allylsulfenamides via [2,3]-Sigmatropic Rearrangement. Eur. J. Org. Chem. 2020, 2020, 6433–6439..
Not in our library10.1002/ejoc.202000961
749.
Baba T.; Takahashi S.; Kambara Y.; Yoshimura A.; Nemykin V. N.; Zhdankin V. V.; Saito A. Development of Imino-λ3-iodanes with Improved Reactivity for Metal-Free [2 + 2+1] Cycloaddition-Type Reactions. Adv. Synth. Catal. 2017, 359, 3860–3864..
Not in our library10.1002/adsc.201700934
750.
Kobayashi Y.; Masakado S.; Takemoto Y. Photoactivated N-Acyliminoiodinanes Applied to Amination: an ortho-Methoxymethyl Group Stabilizes Reactive Precursors. Angew. Chem., Int. Ed. 2018, 57, 693–697..
Not in our library10.1002/anie.201710277
751.
Kimura T.; Hamada S.; Furuta T.; Takemoto Y.; Kobayashi Y. N-Acylimino-λ3-iodanes from the Metathesis of Iodosoarenes and Nitriles for the Photoinduced C-H Perfluoroacylamination of (Hetero)Arenes. Org. Lett. 2022, 24, 4835–4839..
Not in our library10.1021/acs.orglett.2c02054
752.
Guo Y.; Pei C.; Empel C.; Jana S.; Koenigs R. M. Photochemical Nitrene Transfer Reactions of Iminoiodinanes with Sulfides. ChemPhotoChem. 2022, 6, e202100293.
Not in our library10.1002/cptc.202100293
753.
Jurberg I. D.; Nome R. A.; Crespi S.; Atvars T. D. Z.; Konig B. Visible Light-Enhanced C-H Amination of Cyclic Ethers with Iminoiodinanes. Adv. Synth. Catal. 2022, 364, 4061–4068..
Not in our library10.1002/adsc.202201095
754.
Masakado S.; Kobayashi Y.; Takemoto Y. Photo-Induced Aziridination of Alkenes with N-Sulfonyliminoiodinanes. Chem. Pharm. Bull. 2018, 66, 688–690..
Not in our library10.1248/cpb.c18-00198
755.
Guo Y.; Pei C.; Jana S.; Koenigs R. M. Synthesis of Trifluoromethylated Aziridines Via Photocatalytic Amination Reaction. ACS Catal. 2021, 11, 337–342..
Not in our library10.1021/acscatal.0c04564
756.
Mansuy D.; Mahy J. P.; Dureault A.; Bedi G.; Battioni P. Iron- and Manganese-Porphyrin Catalyzed Aziridination of Alkenes by p-Tolylsulfonyl- and Acyliminoiodobenzene. J. Chem. Soc., Chem. Commun. 1984, 1984, 1161–1163..
Not in our library10.1039/c39840001161
757.
Dohi T.; Nakae T.; Takenaga N.; Uchiyama T.; Fukushima K.-i.; Fujioka H.; Kita Y. μ-oxo-Bridged Hypervalent Iodine(III) Compound as an Extreme Oxidant for Aqueous Oxidations. Synthesis 2012, 44, 1183–1189..
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Zhang M.; Chen L.; Liu D.; Liu Z.; Huang J.; Li X.; Yu F. Rh(III)-Catalyzed Cascade Annulation Reaction of N,N-Dimethyl Enaminones with Iodonium Ylides to Give Substituted Isocoumarins. New J. Chem. 2023, 47, 12274–12278..
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Gao Q.-C.; Li Y.-F.; Xuan J.; Hu X.-Q. Practical Synthesis of Isocoumarins via Rh(III)-Catalyzed C-H Activation/Annulation Cascade. Beilstein J. Org. Chem. 2023, 19, 100–106..
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834.
Zhang M.; Chen L.; Liu Z.; Huang J.; Yu F. Unprecedented Chemoselective Ru(III)-Catalyzed [3 + 2] Annulation of Enaminones with Iodonium Ylides for the Synthesis of Functionalized 3a,7a-Dihydroxy Hexahydro-4H-indol-4-ones. Org. Chem. Front. 2023, 10, 5660–5666..
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Kumar S.; Nunewar S.; Kanchupalli V. Rh(III)-Catalyzed Cross-Coupling/Annulation of Two Carbene Precursors: Construction of Dihydrobenzo[c]chromen-6-one Scaffolds and. Asian J. Org. Chem. 2022, 11, e202100689.
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Diaz-Jimenez A.; Kennington S. C. D.; Roglans A.; Pla-Quintana A. Copper(I) Iodide Catalyzed [3 + 3] Annulation of Iodonium Ylides with Pyridinium 1,4-Zwitterionic Thiolates for the Synthesis of 1,4-Oxathiin Scaffolds. Org. Lett. 2023, 25, 4830–4834..
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Li H.; Gu H.; Lu Y.; Xu N.; Han N.; Li J.; Liu J.; Liu J. Synthesis of Tetrahydrocarbazol-4-ones via Rh(III)-Catalyzed C-H Activation/Annulation of Arylhydrazines with Iodonium Ylides. J. Org. Chem. 2022, 87, 8142–8150..
Not in our library10.1021/acs.joc.2c00852
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Zhang M.; Chen L.; Sun H.; Liu Z.; Huang J.; Yu F. Synthesis of Tetrahydro-indolones through Rh(III)-Catalyzed [3 + 2] Annulation of Enaminones with Iodonium Ylides. Org. Lett. 2023, 25, 7298–7303..
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843.
Ren J.; Yang L.; Pi C.; Cui X.; Wu Y. Rhodium(III)-Catalyzed Divergent C-H Functionalization of N-Aryl Amidines with Iodonium Ylides: Access to Carbazolones and Zwitterionic Salts. Adv. Synth. Catal. 2023, 365, 1817–1823..
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844.
Liu C.; Dai Q.; Li Y.; Huang C.; Guo L.; Yang Z. Rh(III)-Catalyzed C-H Annulation of N-Nitrosoanilines with Iodonium Ylides for the Synthesis of N-Alkyl Indoles. J. Org. Chem. 2023, 88, 7281–7289..
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845.
Wang K.; Song X.; Xin Y.; Zhang X.; Fan X. Condition-Controlled Selective Synthesis of Pyranone-Tethered Indazoles or Carbazoles through the Cascade Reactions of N-Nitrosoanilines with Iodonium Ylides. Org. Lett. 2023, 25, 4422–4428..
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846.
Xiong Y.-J.; Shi S.-Q.; Hao W.-J.; Tu S.-J.; Jiang B. A New Dehydrogenative [4 + 1] Annulation between para-Quinone Methides (p-QMs) and Iodonium Ylides for the Synthesis of 2,3-Dihydrobenzofurans. Org. Chem. Front. 2018, 5, 3483–3487..
Not in our library10.1039/c8qo00950c
847.
Mayakrishnan S.; Tamizmani M.; Maheswari N. U. Harnessing Hypervalent Iodonium Ylides as Carbene Precursors: C-H Activation of N-Methoxybenzamides with a Rh(III)-Catalyst. Chem. Commun. 2020, 56, 15462–15465..
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848.
Huang G.; Shan Y.; Yu J.-T.; Pan C. Rhodium-Catalyzed C-H Activation/Cyclization of Aryl Sulfoximines with Iodonium Ylides towards Polycyclic 1,2-Benzothiazines. Org. Biomol. Chem. 2021, 19, 10085–10089..
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849.
Han Z.-P.; Xu M.-M.; Zhang R.-Y.; Xu X.-P.; Ji S.-J. Rh(III)-Catalyzed C(sp2)-H Functionalization/Cyclization Cascade of N-Carboxamide Indole and Iodonium Reagents for Access to Indoloquinazolinone Derivatives. Green Chem. 2021, 23, 6337–6340..
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850.
Yang Z.; Liu J.; Li Y.; Ding J.; Zheng L.; Liu Z.-Q. Three-Component Synthesis of Isoquinolone Derivatives via Rh(III)-Catalyzed C-H Activation and Tandem Annulation. J. Org. Chem. 2022, 87, 14809–14818..
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Nunewar S.; Kumar S.; Priyanka P.; Girase P.; Kanchupalli V. The Solvent-Controlled Rh(III)-Catalyzed Switchable [4 + 2] Annulation of 2-Arylindoles with Iodonium Ylides. Chem. Commun. 2022, 58, 6140–6143..
Not in our library10.1039/d2cc01386j
852.
Nunewar S.; Kumar S.; Meshram A. W.; Kanchupalli V. Ru(II)-Catalyzed C-H Functionalization of 2-Arylbenzimidazoles with Iodonium Ylides: A Straightforward Access to Bridgehead Polycyclic N-Heterocycles. J. Org. Chem. 2022, 87, 13757–13762..
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853.
Liang J.; Huang J.; Yang Q.; Fu Y.; Ding Q.; Peng Y. Synthesis of Dihydroindazolo[2,3-f]phenanthridin-5(6H)-ones via Rh(III)-Catalyzed C-H Activation of 2-Aryl Indazoles and Annulation with Iodonium Ylides. Green Chem. 2022, 24, 8441–8446..
Not in our library10.1039/d2gc03020a
854.
Li R.; Hou Y.-X.; Xu J.-H.; Gao Y.; Hu X.-Q. Divergent Synthesis of Fused N-Heterocycles via Rhodium-Catalysed [4 + 2] Cyclization of Pyrazolidinones with Iodonium Ylides. Org. Chem. Front. 2022, 9, 2181–2186..
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855.
Wen C.; Wang Y.; Yang Y.; Tian Y.-N.; Wang J.; Li S. Hydrazone-oxime Selectively Directed Redox-Neutral [4 + 2] Annulations Cascade with Alkynes and Iodonium Ylides to Build 1,1’-Biisoquinoline Mono-N-oxides. Org. Lett. 2023, 25, 2616–2621..
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856.
Zhao Y.-R.; Li L.; Xuan J. Direct Synthesis of Indolines via Cyclization of Tertiary Aryl Amines with Iodonium Ylides under Sole Visible Light Irradiation. Adv. Synth. Catal. 2023, 365, 110–115..
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857.
Zhao Z.; Luo Y.; Liu S.; Zhang L.; Feng L.; Wang Y. Direct Cyclization of Tertiary Aryl Amines with Iodonium Ylides. Angew. Chem., Int. Ed. 2018, 57, 3792–3796..
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Zhao Z.; Kong X.; Wang W.; Hao J.; Wang Y. Direct Use of Unprotected Aliphatic Amines to Generate N-Heterocycles via β-C-H Malonylation with Iodonium Ylide. Org. Lett. 2020, 22, 230–233..
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Zhang L.; Zhao Z.; Wang W.; Liu S.; Wang Y. Iodonium Ylides Enable the Direct Installation of Hydroxylamines and Oximes into a Broad Range of Alkenes. Org. Lett. 2019, 21, 9171–9174..
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Zhang L.; Kong X.; Liu S.; Zhao Z.; Yu Q.; Wang W.; Wang Y. Succinimide-Promoted Malonylamination of Alkenes with Amines and Iodonium Ylides via Trapping of Transient Aminium Radical Cations. Org. Lett. 2019, 21, 2923–2926..
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Jiang Y.; Li P.; Zhao J.; Liu B.; Li X. Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation. Org. Lett. 2020, 22, 7475–7479..
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Xie P.; Gao H.; Li X.; Jiang Y.; Liu B. Rh(III)-Catalyzed C-C Coupling of Unactivated C(sp3)-H Bonds with Iodonium Ylides for Accessing all-Carbon Quaternary Centers. Org. Chem. Front. 2022, 9, 3823–3827..
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Wu F.; Xiao L.; Xie H.; Chen S.-Y.; Song J.-L.; Zheng Y.-C.; Liu Y.-Z.; Zhang S.-S. Rhodium(III)-Catalyzed Regioselective C(sp2)-H Activation of Indoles at the C4-Position with Iodonium Ylides. Org. Biomol. Chem. 2022, 20, 5055–5059..
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Ren J.; Pi C.; Cui X.; Wu Y. Divergent C(sp2)-H Arylation of Heterocycles via Organic Photoredox Catalysis. Green Chem. 2022, 24, 3017–3022..
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865.
Xu B.; Tambar U. K. Copper-Catalyzed Enantio-, Diastereo-, and Regioselective [2,3]-Rearrangements of Iodonium Ylides. Angew. Chem., Int. Ed. 2017, 56, 9868–9871..
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Xu B.; Gartman J. A.; Tambar U. K. Copper-Catalyzed [1,2]-Rearrangements of Allylic Iodides and Aryl α-Diazoacetates. Tetrahedron 2017, 73, 4150–4159..
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867.
Hock K. J.; Koenigs R. M. Enantioselective [2,3]-Sigmatropic Rearrangements: Metal-Bound or Free Ylides as Reaction Intermediates?. Angew. Chem., Int. Ed. 2017, 56, 13566–13568..
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868.
Xu B.; Tambar U. K. Ligand-Controlled Regiodivergence in the Copper-Catalyzed [2,3]- and [1,2]-Rearrangements of Iodonium Ylides. J. Am. Chem. Soc. 2016, 138, 12073–12076..
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869.
Chasse M.; Pees A.; Lindberg A.; Liang S. H.; Vasdev N. Spirocyclic Iodonium Ylides for Fluorine-18 Radiolabeling of Non-Activated Arenes: From Concept to Clinical Research. Chem. Rec. 2023, 23, e202300072.
Not in our library10.1002/tcr.202300072
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Kruell J.; Heinrich M. R. [18F]Fluorine-Labeled Pharmaceuticals: Direct Aromatic Fluorination Compared to Multi-Step Strategies. Asian J. Org. Chem. 2019, 8, 576–590..
Not in our library10.1002/ajoc.201800494
871.
Jakobsson J. E.; Groennevik G.; Riss P. J. Organocatalyst-Assisted Ar-18F Bond Formation: a Universal Procedure for Direct Aromatic Radiofluorination. Chem. Commun. 2017, 53, 12906–12909..
Not in our library10.1039/c7cc07211b
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Petersen I. N.; Villadsen J.; Hansen H. D.; Madsen J.; Jensen A. A.; Gillings N.; Lehel S.; Herth M. M.; Knudsen G. M.; Kristensen J. L. 18F-Labelling of Electron Rich Iodonium Ylides: Application to the Radiosynthesis of Potential 5-HT2A Receptor PET Ligands. Org. Biomol. Chem. 2017, 15, 4351–4358..
Not in our library10.1039/c7ob00628d
873.
Wang L.; Cheng R.; Vasdev N.; Liang S. H.; Cheng R.; Du Y.; Fujinaga M.; Zhang Y.; Hatori A.; Kumata K.; Zhang M.-R.; Yang J.; Yang J.; Ran C. A Facile Radiolabeling of [(18)F]FDPA via Spirocyclic Iodonium Ylides: Preliminary PET Imaging Studies in Preclinical Models of Neuroinflammation. J. Med. Chem. 2017, 60, 5222–5227..
Not in our library10.1021/acs.jmedchem.7b00432
874.
Cheng R.; Mori W.; Ma L.; Alhouayek M.; Hatori A.; Zhang Y.; Ogasawara D.; Yuan G.; Chen Z.; Zhang X.; Shi H.; Yamasaki T.; Xie L.; Kumata K.; Fujinaga M.; Nagai Y.; Minamimoto T.; Svensson M.; Wang L.; Du Y.; Ondrechen M. J.; Vasdev N.; Cravatt B. F.; Fowler C.; Zhang M.-R.; Liang S. H. In Vitro and in Vivo Evaluation of 11C-Labeled Azetidinecarboxylates for Imaging Monoacylglycerol Lipase by PET Imaging Studies. J. Med. Chem. 2018, 61, 2278–2291..
Not in our library10.1021/acs.jmedchem.7b01400
875.
Fujinaga M.; Kumata K.; Zhang Y.; Hatori A.; Yamasaki T.; Mori W.; Ohkubo T.; Xie L.; Nengaki N.; Zhang M.-R. Synthesis of Two Novel [18f]Fluorobenzene-Containing Radiotracers via Spirocyclic Iodonium Ylides and Positron Emission Tomography Imaging of Translocator Protein (18 kDa) in Ischemic Brain. Org. Biomol. Chem. 2018, 16, 8325–8335..
Not in our library10.1039/c8ob01700j
876.
Kumata K.; Zhang Y.; Fujinaga M.; Ohkubo T.; Mori W.; Yamasaki T.; Hanyu M.; Xie L.; Hatori A.; Zhang M.-R. [18F]DAA1106: Automated Radiosynthesis Using Spirocyclic Iodonium Ylide and Preclinical Evaluation for Positron Emission Tomography Imaging of Translocator Protein (18 kDa). Bioorg. Med. Chem. 2018, 26, 4817–4822..
Not in our library10.1016/j.bmc.2018.08.017
877.
Baum E.; Zhang W.; Li S.; Cai Z.; Holden D.; Huang Y. A Novel 18F-Labeled Radioligand for Positron Emission Tomography Imaging of 11β-Hydroxysteroid Dehydrogenase (11β-HSD1): Synthesis and Preliminary Evaluation in Nonhuman Primates. ACS Chem. Neurosci. 2019, 10, 2450–2458..
Not in our library10.1021/acschemneuro.8b00715
878.
Liang S. H.; Wang L.; Stephenson N. A.; Rotstein B. H.; Vasdev N. Facile 18F Labeling of Non-Activated Arenes via a Spirocyclic Iodonium(III) Ylide Method and its Application in Tthe Synthesis of the mGluR5 PET Radiopharmaceutical [18F]FPEB. Nat. Protoc. 2019, 14, 1530–1545..
Not in our library10.1038/s41596-019-0149-3
879.
Petersen I. N.; Madsen J.; Poulie C. B. M.; Kjaer A.; Herth M. M. One-Step Synthesis of N-Succinimidyl-4-[18F]fluorobenzoate ([18F]SFB). Molecules 2019, 24, 3436.
Not in our library10.3390/molecules24193436
880.
Il’in V. A.; Pyzhik E. V.; Balakhonov A. B.; Kiryushin M. A.; Shcherbatova E. V.; Kuznetsov A. A.; Kostin P. A.; Golovin A. V.; Korshun V. A.; Brylev V. A.; Sapozhnikova K. A.; Kopylov A. M.; Pavlova G. V.; Pronin I. N. Radiochemical Synthesis of 4-[18F]FluorobenzylAzide and Its Conjugation with EGFR-Specific Aptamers. Molecules 2023, 28, 294.
Not in our library10.3390/molecules28010294
881.
Nabar K. U.; Bhanage B. M.; Dawande S. G. Copper-Catalyzed N-Arylation of Amines with Aryliodonium Ylides in Water. Beilstein J. Org. Chem. 2023, 19, 1008–1014..
Not in our library10.3762/bjoc.19.76
882.
Hartmann M.; Li Y.; Mueck-Lichtenfeld C.; Studer A. Generation of Aryl Radicals through Reduction of Hypervalent Iodine(III) Compounds with TEMPONa: Radical Alkene Oxyarylation. Chem. - Eur. J. 2016, 22, 3485–3490..
Not in our library10.1002/chem.201504852
883.
Chen J.-Y.; Wu H.-Y.; Song H.-Y.; Li H.-X.; Jiang J.; Yang T.-B.; He W.-M. Visible-Light-Induced Annulation of Iodonium Ylides and 2-Isocyanobiaryls to Access 6-Arylated Phenanthridines. J. Org. Chem. 2023, 88, 8360–8368..
Not in our library10.1021/acs.joc.3c00380
884.
Joshi A.; De S. R. Diaryliodonium Salts in Transition-Metal-Catalyzed Chelation-Induced C(sp2/sp3)-H Arylations. Eur. J. Org. Chem. 2021, 2021, 1837–1858..
Not in our library10.1002/ejoc.202100066
885.
Beke F.; Csenki J. T.; Novak Z. Fluoroalkylations and Fluoroalkenylations with Iodonium Salts. Chem. Rec. 2023, 23, e202300083.
Not in our library10.1002/tcr.202300083
886.
Hashishin T.; Osawa T.; Miyamoto K.; Uchiyama M. Practical Synthesis of Ethynyl(phenyl)-λ3-Iodane Using Calcium Carbide as an Ethynyl Group Source. Front. Chem. 2020, 8, 12.
Not in our library10.3389/fchem.2020.00012
887.
Han J.-B.; Yang L.; Chen X.; Zha G.-F.; Zhang C.-P. Perfluoroalkanesulfonylation of Alkynyl(phenyl)iodonium Tosylates by the Weakly Nucleophilic Sodium Perfluoroalkanesulfinates. Adv. Synth. Catal. 2016, 358, 4119–4124..
Not in our library10.1002/adsc.201600717
888.
Rodriguez A.; Moran W. J. Preparation of Alkyl Alkynyl Sulfones and Cyclic Vinyl Sulfones from Alkynyl(aryl)iodonium Salts. J. Org. Chem. 2016, 81, 2543–2548..
Not in our library10.1021/acs.joc.6b00124
889.
Toriumi N.; Asano N.; Miyamoto K.; Muranaka A.; Uchiyama M. N-Alkynylpyridinium Salts: Highly Electrophilic Alkyne-Pyridine Conjugates as Precursors of Cationic Nitrogen-Embedded Polycyclic Aromatic Hydrocarbons. J. Am. Chem. Soc. 2018, 140, 3858–3862..
Not in our library10.1021/jacs.8b00356
890.
Al-Huniti M. H.; Sullivan Z. B.; Stanley J. L.; Carson J. A.; Hyatt I. F. D.; Hairston A. C.; Croatt M. P. Hypervalent Iodonium Alkynyl Triflate Generated Phenylcyanocarbene and Its Reactivity with Aromatic Systems. J. Org. Chem. 2017, 82, 11772–11780..
Not in our library10.1021/acs.joc.7b01608
891.
Rajkiewicz A. A.; Wojciechowska N.; Kalek M. N-Heterocyclic Carbene-Catalyzed Synthesis of Ynones via C-H Alkynylation of Aldehydes with Alkynyliodonium Salts - Evidence for Alkynyl Transfer via Direct Substitution at Acetylenic Carbon. ACS Catal. 2020, 10, 831–841..
Not in our library10.1021/acscatal.9b04394
892.
Miyamoto K.; Narita S.; Masumoto Y.; Hashishin T.; Osawa T.; Kimura M.; Ochiai M.; Uchiyama M. Room-Temperature Chemical Synthesis of C2. Nat. Commun. 2020, 11, 2134.
Not in our library10.1038/s41467-020-16025-x
893.
Rzepa H. S.; Arita M.; Miyamoto K.; Uchiyama M. A Combined DFT-Predictive and Experimental Exploration of the Sensitivity towards Nucleofuge Variation in Zwitterionic Intermediates Relating to Mechanistic Models for Unimolecular Chemical Generation and Trapping of Free C2 and Alternative Bimolecular Pathways Involving no Free C2. Phys. Chem. Chem. Phys. 2022, 24, 25816–25821..
Not in our library10.1039/d2cp01214f
894.
Gorantla S. M. N. V. T.; Pan S.; Chandra Mondal K.; Frenking G. Bonding Analysis of the C2 Precursor Me3E-C2-I(Ph)FBF3 (E = C, Si, Ge). Pure Appl. Chem. 2022, 94, 767–781..
Not in our library10.1515/pac-2021-1102
895.
Rzepa H. S. Routes Involving no Free C2 in a DFT-Computed Mechanistic Model for the Reported Room-Temperature Chemical Synthesis of C2. Phys. Chem. Chem. Phys. 2021, 23, 12630–12636..
Not in our library10.1039/d1cp02056k
896.
Kagami K.; Liang X.; Ishibashi N.; Ohrui S.; Tayu M.; Saito N. Synthesis of N-(Acyloxy)-N-alkynylamides via Generation of ″C2″ from Hypervalent Alkynyliodane and a Weak Base. Chem. Commun. 2023, 59, 8274–8277..
Not in our library10.1039/d3cc01403g
897.
Matsumoto T.; Hagiyama H.; Kuribayashi K.; Hioki K.; Fujita H.; Ochiai M.; Kunishima M. A Versatile Iodo(III)etherification of Terminal Ethynylsilanes using BF3-OiPr2 and Alkyl Benzyl Ethers. Org. Biomol. Chem. 2021, 19, 3825–3828..
Not in our library10.1039/d1ob00479d
898.
Zawia E.; Hamnett D. J.; Moran W. J. Preparation and Synthetic Utility of Stable 1,3-Enynyl- and 1,3-Dienyl(aryl)iodonium Salts. J. Org. Chem. 2017, 82, 3960–3964..
Not in our library10.1021/acs.joc.7b00192
899.
Zawia E.; Moran W. J. Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides. Molecules 2016, 21, 1073–1083..
Not in our library10.3390/molecules21081073
900.
Shin M.; Kim M.; Hwang C.; Lee H.; Kwon H.; Park J.; Lee E.; Cho S. H. Facile Synthesis of α-Boryl-Substituted Allylboronate Esters Using Stable Bis[(pinacolato)boryl]methylzinc Reagents. Org. Lett. 2020, 22, 2476–2480..
Not in our library10.1021/acs.orglett.0c00721
901.
Zhu D.; Gan S.; Bao R. L.-Y.; Shi L. Copper-Catalyzed Cross-Coupling of Vinyliodonium Salts and Diboron Reagents to Generate Alkenyl Boronic Esters. Org. Biomol. Chem. 2020, 18, 5567–5570..
Not in our library10.1039/d0ob01121e
902.
Yuan H.; Guo L.; Liu F.; Miao Z.; Feng L.; Gao H. Copper-Catalyzed Tandem O-Vinylation of Arylhydroxylamines/[3,3]-Rearrangement/Cyclization: Synthesis of Highly Substituted Indoles and Benzoindoles. ACS Catal. 2019, 9, 3906–3912..
Not in our library10.1021/acscatal.9b00470
903.
Zhang L.; Oestreich M. Copper-Catalyzed Cross-Coupling of Vinyliodonium Salts and Zinc-Based Silicon Nucleophiles. Org. Lett. 2018, 20, 8061–8063..
Not in our library10.1021/acs.orglett.8b03714
904.
Sheng J.; Wang Y.; Su X.; He R.; Chen C. Copper-Catalyzed [2 + 2+2] Modular Synthesis of Multisubstituted Pyridines: Alkenylation of Nitriles with Vinyliodonium Salts. Angew. Chem., Int. Ed. 2017, 56, 4824–4828..
Not in our library10.1002/anie.201700696
905.
Pankajakshan S.; Ang W. L.; Sreejith S.; Stuparu M. C.; Loh T.-P. Aerobic Copper Catalysis for Tandem Oxy-N-alkenylation of [1,2,3]Triazolo[1,5-a]pyridines. Adv. Synth. Catal. 2016, 358, 3034–3038..
Not in our library10.1002/adsc.201600580
906.
Teskey C. J.; Sohel S. M. A.; Bunting D. L.; Modha S. G.; Greaney M. F. Domino N-/C-Arylation via In Situ Generation of a Directing Group: Atom-Efficient Arylation Using Diaryliodonium Salts. Angew. Chem., Int. Ed. 2017, 56, 5263–5266..
Not in our library10.1002/anie.201701523
907.
Jana S.; Telu S.; Yang B. Y.; Haskali M. B.; Jakobsson J. E.; Pike V. W. Rapid Syntheses of [11C]Arylvinyltrifluoromethanes through Treatment of (E)-Arylvinyl(phenyl)iodonium Tosylates with [11C]Trifluoromethylcopper(I). Org. Lett. 2020, 22, 4574–4578..
Not in our library10.1021/acs.orglett.0c01705
908.
Frost A. B.; Brambilla M.; Exner R. M.; Tredwell M. Synthesis and Derivatization of 1,1-[18F]Difluorinated Alkenes. Angew. Chem., Int. Ed. 2019, 58, 472–476..
Not in our library10.1002/anie.201810413
909.
Toth B. L.; Salyi G.; Domjan A.; Egyed O.; Benyei A.; Gonda Z.; Novak Z. Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C-H Activation. Adv. Synth. Catal. 2022, 364, 348–354..
Not in our library10.1002/adsc.202101108
910.
Ren W.; Xiang H.; Peng C.; Musha Z.; Chen J.; Li X.; Huang R.; Hu Y. Direct C-H Functionalization of Difluoroboron Dipyrromethenes (BODIPYs) at β-Position by Iodonium Salts. RSC Adv. 2018, 8, 5542–5549..
Not in our library10.1039/c7ra13070h
911.
Rajkiewicz A. A.; Kalek M. N-Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts To Generate α,β-Unsaturated Ketones. Org. Lett. 2018, 20, 1906–1909..
Not in our library10.1021/acs.orglett.8b00447
912.
Liu C.; Wang Q. Arylation, Vinylation, and Alkynylation of Electron-Deficient (Hetero)arenes Using Iodonium Salts. Org. Lett. 2016, 18, 5118–5121..
Not in our library10.1021/acs.orglett.6b02550
913.
Liu C.; Wang Q. Alkenylation of C(sp3)-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts. Angew. Chem., Int. Ed. 2018, 57, 4727–4731..
Not in our library10.1002/anie.201713278
914.
Meszaros A.; Szekely A.; Stirling A.; Novak Z. Design of Trifluoroalkenyl Iodonium Salts for a Hypervalency-Aided Alkenylation-Cyclization Strategy: Metal-Free Construction of Aziridine Rings. Angew. Chem., Int. Ed. 2018, 57, 6643–6647..
Not in our library10.1002/anie.201802347
915.
Maiti S.; Kim J.; Park J.-H.; Nam D.; Lee J. B.; Kim Y.-J.; Kee J.-M.; Seo J. K.; Myung K.; Rohde J.-U.; Choe W.; Kwon O.-H.; Hong S. Y. Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability. J. Org. Chem. 2019, 84, 6737–6751..
Not in our library10.1021/acs.joc.9b00470
916.
Zhao C.-L.; Han Q.-Y.; Zhang C.-P. TfOH-Promoted Transition-Metal-Free Cascade Trifluoroethylation/Cyclization of Organic Isothiocyanates by Phenyl(2,2,2-trifluoroethyl)iodonium Triflate. Org. Lett. 2018, 20, 6480–6484..
Not in our library10.1021/acs.orglett.8b02793
917.
Zhao C.-L.; Yang J.; Han Z.-Z.; Zhang C.-P. Structure-Dependent Selective O- or C-Trifluoroethylation of 1,3-Dicarbonyls by Mesityl(2,2,2-Trifluoroethyl)Iodonium Triflate. J. Fluorine Chem. 2017, 204, 23–30..
Not in our library10.1016/j.jfluchem.2017.09.009
918.
Niu Y.; Cao C. K.; Ge C.; Qu H.; Chen C. The Pd-Catalyzed Synthesis of Difluoroethyl and Difluorovinyl Compounds with a Chlorodifluoroethyl Iodonium Salt (CDFI). Chin. Chem. Lett. 2022, 33, 1541–1544..
Not in our library10.1016/j.cclet.2021.09.004
919.
Han Q.-Y.; Hu X.; Xue X.-S.; Zhao C.-L.; Zhang C.-P. Palladium-Catalyzed Trifluoroethylation of Benzo[h]quinoline Derivatives by Mesityl(2,2,2-trifluoroethyl)iodonium Triflate. Asian J. Org. Chem. 2019, 8, 665–670..
Not in our library10.1002/ajoc.201900030
920.
Maraswami M.; Pankajakshan S.; Chen G.; Loh T.-P. Palladium-Catalyzed Direct C-H Trifluoroethylation of Aromatic Amides. Org. Lett. 2017, 19, 4223–4226..
Not in our library10.1021/acs.orglett.7b01859
921.
Toth B. L.; Kovacs S.; Salyi G.; Novak Z. Mild and Efficient Palladium-Catalyzed Direct Trifluoroethylation of Aromatic Systems by C-H Activation. Angew. Chem., Int. Ed. 2016, 55, 1988–1992..
Not in our library10.1002/anie.201510555
922.
Csenki J. T.; Toth B. L.; Beke F.; Varga B. P.; Feher P. P.; Stirling A.; Czegeny Z.; Benyei A.; Novak Z. Synthesis of Hydrofluoroolefin-Based Iodonium Reagent via Dyotropic Rearrangement and Its Utilization in Fluoroalkylation. Angew. Chem., Int. Ed. 2022, 61, e202208420.
Not in our library10.1002/anie.202208420
923.
Stuart D. R. Unsymmetrical Diaryliodonium Salts as Aryne Synthons: Renaissance of a C-H Deprotonative Approach to Arynes. Synlett 2017, 28, 275–279..
Not in our library10.1055/s-0036-1588683
924.
Cao C. K.; Sheng J.; Chen C. Cu-Catalyzed Cascade Annulation of Diaryliodonium Salts and Nitriles: Synthesis of Nitrogen-Containing Heterocycles. Synthesis 2017, 49, 5081–5092..
Not in our library10.1055/s-0036-1589515
925.
Merritt E. A.; Olofsson B. Diaryliodonium Salts: A Journey from Obscurity to Fame. Angew. Chem., Int. Ed. 2009, 48, 9052–9070..
Not in our library10.1002/anie.200904689
926.
Linde E.; Mondal S.; Olofsson B. Advancements in the Synthesis of Diaryliodonium Salts: Updated Protocols. Adv. Synth. Catal. 2023, 365, 2751–2756..
Not in our library10.1002/adsc.202300354
927.
Di Tommaso E. M.; Walther M.; Staubitz A.; Olofsson B. Ortho-Functionalization of Azobenzenes via Hypervalent Iodine Reagents. Chem. Commun. 2023, 59, 5047–5050..
Not in our library10.1039/d3cc01060k
928.
Linde E.; Knippenberg N.; Olofsson B. Synthesis of Cyclic and Acyclic ortho-Aryloxy Diaryliodonium Salts for Chemoselective Functionalizations. Chem. - Eur. J. 2022, 28, e202202453.
Not in our library10.1002/chem.202202453
929.
Karandikar S. S.; Stuart D. R. Refining Boron-Iodane Exchange to Access Versatile Arylation Reagents. Chem. Commun. 2022, 58, 1211–1214..
Not in our library10.1039/d1cc06341c
930.
Zhou J.; Bao Z.; Wu P.; Chen C. Preparation and Synthetic Application of Naproxen-Containing Diaryliodonium Salts. Molecules 2021, 26, 3240.
Not in our library10.3390/molecules26113240
931.
Mikhael M.; Guo W.; Tantillo D. J.; Wengryniuk S. E. Umpolung Strategy for Arene C-H Etherification Leading to Functionalized Chromanes Enabled by I(III) N-Ligated Hypervalent Iodine Reagents. Adv. Synth. Catal. 2021, 363, 4867–4875..
Not in our library10.1002/adsc.202100809
932.
Soldatova N. S.; Postnikov P. S.; Yusubov M. S.; Wirth T. Flow Synthesis of Iodonium Trifluoroacetates through Direct Oxidation of Iodoarenes by Oxone. Eur. J. Org. Chem. 2019, 2019, 2081–2088..
Not in our library10.1002/ejoc.201900220
933.
Dohi T.; Hayashi T.; Ueda S.; Shoji T.; Komiyama K.; Takeuchi H.; Kita Y. Recyclable Synthesis of Mesityl Iodonium(III) Salts. Tetrahedron 2019, 75, 3617–3627..
Not in our library10.1016/j.tet.2019.05.033
934.
Yoshimura A.; Shea M. T.; Guselnikova O.; Postnikov P. S.; Rohde G. T.; Saito A.; Yusubov M. S.; Nemykin V. N.; Zhdankin V. V. Preparation and Structure of Phenolic Aryliodonium Salts. Chem. Commun. 2018, 54, 10363–10366..
Not in our library10.1039/c8cc06211k
935.
Lindstedt E.; Reitti M.; Olofsson B. One-Pot Synthesis of Unsymmetric Diaryliodonium Salts from Iodine and Arenes. J. Org. Chem. 2017, 82, 11909–11914..
Not in our library10.1021/acs.joc.7b01652
936.
Yuan Z.; Cheng R.; Chen P.; Liu G.; Liang S. H. Efficient Pathway for the Preparation of Aryl(isoquinoline)iodonium(III) Salts and Synthesis of Radiofluorinated Isoquinolines. Angew. Chem., Int. Ed. 2016, 55, 11882–11886..
Not in our library10.1002/anie.201606381
937.
Laudadio G.; Gemoets H. P. L.; Hessel V.; Noel T. Flow Synthesis of Diaryliodonium Triflates. J. Org. Chem. 2017, 82, 11735–11741..
Not in our library10.1021/acs.joc.7b01346
938.
Das P.; Shibata N. Electrophilic Triflyl-arylation and Triflyl-pyridylation by Unsymmetrical Aryl/Pyridyl-λ3-iodonium Salts: Synthesis of Aryl and Pyridyl Triflones. J. Org. Chem. 2017, 82, 11915–11924..
Not in our library10.1021/acs.joc.7b01690
939.
Carreras V.; Sandtorv A. H.; Stuart D. R. Synthesis of Aryl(2,4,6-trimethoxyphenyl)iodonium Trifluoroacetate Salts. J. Org. Chem. 2017, 82, 1279–1284..
Not in our library10.1021/acs.joc.6b02811
940.
One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone–sulfuric acid · 2018
Not checked
941.
Aliyarova I. S.; Tupikina E. Y.; Soldatova N. S.; Ivanov D. M.; Postnikov P. S.; Yusubov M.; Kukushkin V. Y. Halogen Bonding Involving Gold Nucleophiles in Different Oxidation States. Inorg. Chem. 2022, 61, 15398–15407..
Not in our library10.1021/acs.inorgchem.2c01858
942.
Suslonov V. V.; Soldatova N. S.; Ivanov D. M.; Galmes B.; Frontera A.; Resnati G.; Postnikov P. S.; Kukushkin V. Y.; Bokach N. A. Diaryliodonium Tetrachloroplatinates(II): Recognition of a Trifurcated Metal-Involving μ3-I···(Cl,Cl,Pt) Halogen Bond. Cryst. Growth Des. 2021, 21, 5360–5372..
Not in our library10.1021/acs.cgd.1c00654
943.
Soldatova N. S.; Postnikov P. S.; Suslonov V. V.; Kissler T. Y.; Ivanov D. M.; Yusubov M. S.; Galmes B.; Frontera A.; Kukushkin V. Y. Diaryliodonium as a Double σ-Hole Donor: the Dichotomy of Thiocyanate Halogen Bonding Provides Divergent Solid State Arylation by Diaryliodonium Cations. Org. Chem. Front. 2020, 7, 2230–2242..
Not in our library10.1039/d0qo00678e
944.
Ye B.; Zhao J.; Zhao K.; McKenna J. M.; Toste F. D. Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective α-C(sp3)-H Acetalization. J. Am. Chem. Soc. 2018, 140, 8350–8356..
Not in our library10.1021/jacs.8b05962
945.
Labattut A.; Tremblay P.-L.; Moutounet O.; Legault C. Y. Experimental and Theoretical Quantification of the Lewis Acidity of Iodine(III) Species. J. Org. Chem. 2017, 82, 11891–11896..
Not in our library10.1021/acs.joc.7b01616
946.
Mayer R. J.; Ofial A. R.; Mayr H.; Legault C. Y. Lewis Acidity Scale of Diaryliodonium Ions toward Oxygen, Nitrogen, and Halogen Lewis Bases. J. Am. Chem. Soc. 2020, 142, 5221–5233..
Not in our library10.1021/jacs.9b12998
947.
Lukamto D. H.; Gaunt M. J. Enantioselective Copper-Catalyzed Arylation-Driven Semipinacol Rearrangement of Tertiary Allylic Alcohols with Diaryliodonium Salts. J. Am. Chem. Soc. 2017, 139, 9160–9163..
Not in our library10.1021/jacs.7b05340
948.
Garad D. N.; Viveki A. B.; Mhaske S. B. Pd-Catalyzed Regioselective Mono-Arylation: Quinazolinone as the Inherent Directing Group for C(sp2)-H Activation. J. Org. Chem. 2017, 82, 6366–6372..
Not in our library10.1021/acs.joc.7b00948
949.
Yang M.-N.; Yan D.-M.; Zhao Q.-Q.; Chen J.-R.; Xiao W.-J. Synthesis of Dihydropyrazoles via Ligand-Free Pd-Catalyzed Alkene Aminoarylation of Unsaturated Hydrazones with Diaryliodonium Salts. Org. Lett. 2017, 19, 5208–5211..
Not in our library10.1021/acs.orglett.7b02480
950.
Li X.; Chen P.; Liu G. Palladium-Catalyzed Intermolecular Arylcarbonylation of Unactivated Alkenes: Incorporation of Bulky Aryl Groups at Room Temperature. Angew. Chem., Int. Ed. 2018, 57, 15871–15876..
Not in our library10.1002/anie.201810405
951.
Yi D.; Zhu F.; Walczak M. A. Glycosyl Cross-Coupling with Diaryliodonium Salts: Access to Aryl C-Glycosides of Biomedical Relevance. Org. Lett. 2018, 20, 1936–1940..
Not in our library10.1021/acs.orglett.8b00475
952.
Ghosh M. K.; Rzymkowski J.; Kalek M. Transition-Metal-Free Aryl-Aryl Cross-Coupling: C-H Arylation of 2-Naphthols with Diaryliodonium Salts. Chem. - Eur. J. 2019, 25, 9619–9623..
Not in our library10.1002/chem.201902204
953.
Perez-Saavedra B.; Vazquez-Galinanes N.; Saa C.; Fananas-Mastral M. Copper(I)-Catalyzed Tandem Carboarylation/Cyclization of Alkynyl Phosphonates with Diaryliodonium Salts. ACS Catal. 2017, 7, 6104–6109..
Not in our library10.1021/acscatal.7b02434
954.
Niu Y.; Qi Z.; Lou Q.; Bai P.; Yang S. Copper-Catalyzed Arylation of Polycyclic Aromatic Hydrocarbons by the P = O Group. Chem. Commun. 2020, 56, 14721–14724..
Not in our library10.1039/d0cc06639g
955.
Xu Q.; Zhang H.; Ge F.-B.; Wang X.-M.; Zhang P.; Lu C.-J.; Liu R.-R. Cu(I)-Catalyzed Asymmetric Arylation of Pyrroles with Diaryliodonium Salts toward the Synthesis of N-N Atropisomers. Org. Lett. 2022, 24, 3138–3143..
Not in our library10.1021/acs.orglett.2c00812
956.
Sun Z.; Dai M.; Ding C.; Chen S.; Chen L.-A. Regiodivergent and Stereoselective Synthesis of Highly Substituted 1,3-Dienes via Arylative Acyloxy Migration of Propargyl Esters. J. Am. Chem. Soc. 2023, 145, 18115–18125..
Not in our library10.1021/jacs.3c06253
957.
Chen H.; Wang L.; Han J. Aryl Radical-Induced Desulfonylative ipso-Substitution of Diaryliodonium Salts: an Efficient Route to Sterically Hindered Biarylamines. Chem. Commun. 2020, 56, 5697–5700..
Not in our library10.1039/d0cc01766c
958.
Lei G.; Zhang H.; Chen B.; Xu M.; Zhang G. Copper-catalyzed Enantioselective Arylalkynylation of Alkenes. Chem. Sci. 2020, 11, 1623–1628..
Not in our library10.1039/c9sc04029c
959.
Saikia R. A.; Dutta A.; Sarma B.; Thakur A. J. Metal-Free Regioselective N2-Arylation of 1H-Tetrazoles with Diaryliodonium Salts. J. Org. Chem. 2022, 87, 9782–9796..
Not in our library10.1021/acs.joc.2c00848
960.
Kikushima K.; Miyamoto N.; Watanabe K.; Koseki D.; Kita Y.; Dohi T. Ligand- and Counterion-Assisted Phenol O-Arylation with TMP-Iodonium(III) Acetates. Org. Lett. 2022, 24, 1924–1928..
Not in our library10.1021/acs.orglett.2c00294
961.
Katagiri K.; Kuriyama M.; Yamamoto K.; Demizu Y.; Onomura O. Organocatalytic Synthesis of Phenols from Diaryliodonium Salts with Water under Metal-Free Conditions. Org. Lett. 2022, 24, 5149–5154..
Not in our library10.1021/acs.orglett.2c01989
962.
Kervefors G.; Pal K. B.; Tolnai G. L.; Mahanti M.; Leffler H.; Nilsson U. J.; Olofsson B. Synthesis and Biological Studies of O3-Aryl Galactosides as Galectin Inhibitors. Helv. Chim. Acta 2021, 104, e2000220.
Not in our library10.1002/hlca.202000220
963.
Kervefors G.; Kersting L.; Olofsson B. Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts. Chem. - Eur. J. 2021, 27, 5790–5795..
Not in our library10.1002/chem.202005351
964.
Meng H.; Wen L.; Xu Z.; Li Y.; Hao J.; Zhao Y. Nonafluoro-tert-butoxylation of Diaryliodonium Salts. Org. Lett. 2019, 21, 5206–5210..
Not in our library10.1021/acs.orglett.9b01813
965.
Li S.; Lv H.; Yu Y.; Ye X.; Li B.; Yang S.; Mo Y.; Kong X. Domino N-/C- or N-/N-/C-Arylation of Imidazoles to Yield Polyaryl Imidazolium Salts via Atom-Economical Use of Diaryliodonium Salts. Chem. Commun. 2019, 55, 11267–11270..
Not in our library10.1039/c9cc05237b
966.
Villo P.; Kervefors G.; Olofsson B. Transition Metal-Free, Chemoselective Arylation of Thioamides Yielding Aryl Thioimidates or N-Aryl Thioamides. Chem. Commun. 2018, 54, 8810–8813..
Not in our library10.1039/c8cc04795b
967.
Reitti M.; Gurubrahamam R.; Walther M.; Lindstedt E.; Olofsson B. Synthesis of Phenols and Aryl Silyl Ethers via Arylation of Complementary Hydroxide Surrogates. Org. Lett. 2018, 20, 1785–1788..
Not in our library10.1021/acs.orglett.8b00287
968.
Purkait N.; Kervefors G.; Linde E.; Olofsson B. Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions. Angew. Chem., Int. Ed. 2018, 57, 11427–11431..
Not in our library10.1002/anie.201807001
969.
Shi W.-M.; Li X.-H.; Liang C.; Mo D.-L. Base-Free Selective O-Arylation and Sequential [3,3]-Rearrangement of Amidoximes with Diaryliodonium Salts: Synthesis of 2-Substituted Benzoxazoles. Adv. Synth. Catal. 2017, 359, 4129–4135..
Not in our library10.1002/adsc.201700906
970.
Dohi T.; Koseki D.; Sumida K.; Okada K.; Mizuno S.; Kato A.; Morimoto K.; Kita Y. Metal-Free O-Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated in situ from Iodosoarenes. Adv. Synth. Catal. 2017, 359, 3503–3508..
Not in our library10.1002/adsc.201700843
971.
Tolnai G. L.; Nilsson U. J.; Olofsson B. Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents. Angew. Chem., Int. Ed. 2016, 55, 11226–11230..
Not in our library10.1002/anie.201605999
972.
Reitti M.; Villo P.; Olofsson B. One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts. Angew. Chem., Int. Ed. 2016, 55, 8928–8932..
Not in our library10.1002/anie.201603175
973.
Lucchetti N.; Scalone M.; Fantasia S.; Muniz K. Sterically Congested 2,6-Disubstituted Anilines from Direct C-N Bond Formation at an Iodine(III) Center. Angew. Chem., Int. Ed. 2016, 55, 13335–13339..
Not in our library10.1002/anie.201606599
974.
Orlovskaya V. V.; Fedorova O. S.; Viktorov N. B.; Vaulina D. D.; Krasikova R. N. One-Pot Radiosynthesis of [18F]Anle138b-5-(3-Bromophenyl)-3-(6-[18F]fluorobenzo[d][1,3]dioxol-5-yl)-1H-pyrazole-A Potential PET Radiotracer Targeting α-Synuclein Aggregates. Molecules 2023, 28, 2732.
Not in our library10.3390/molecules28062732
975.
Pauton M.; Gillet R.; Aubert C.; Bluet G.; Gruss-Leleu F.; Roy S.; Perrio C. The First Radiosynthesis of 2-Amino-5-[18F]fluoropyridines via a ″Minimalist″ Radiofluorination/Palladium-Catalyzed Amination Sequence from Anisyl(2-Bromopyridinyl)Iodonium Triflate. Org. Biomol. Chem. 2019, 17, 6359–6363..
Not in our library10.1039/c9ob01187k
976.
Orlovskaya V. V.; Modemann D. J.; Kuznetsova O. F.; Fedorova O. S.; Urusova E. A.; Kolks N.; Neumaier B.; Krasikova R. N.; Zlatopolskiy B. D. Alcohol-Supported Cu-Mediated 18F-Fluorination of Iodonium Salts Under ″Minimalist″ Conditions. Molecules 2019, 24, 3197.
Not in our library10.3390/molecules24173197
977.
Kwon Y.-D.; Son J.; Chun J.-H. Chemoselective Radiosyntheses of Electron-Rich [18F]Fluoroarenes from Aryl(2,4,6-trimethoxyphenyl)iodonium Tosylates. J. Org. Chem. 2019, 84, 3678–3686..
Not in our library10.1021/acs.joc.9b00019
978.
Masumoto Y.; Miyamoto K.; Iuchi T.; Ochiai M.; Hirano K.; Saito T.; Wang C.; Uchiyama M. Mechanistic Study on Aryl-Exchange Reaction of Diaryl-λ3-iodane with Aryl Iodide. J. Org. Chem. 2018, 83, 289–295..
Not in our library10.1021/acs.joc.7b02701
979.
McCammant M. S.; Thompson S.; Brooks A. F.; Krska S. W.; Scott P. J. H.; Sanford M. S. Cu-Mediated C-H 18F-Fluorination of Electron-Rich (Hetero)arenes. Org. Lett. 2017, 19, 3939–3942..
Not in our library10.1021/acs.orglett.7b01902
980.
Zhou D.; Kim S. H.; Chu W.; Voller T.; Katzenellenbogen J. A. Evaluation of Aromatic Radiobromination by Nucleophilic Substitution Using Diaryliodonium Salt Precursors. J. Labelled Compd. Radiopharm. 2017, 60, 450–456..
Not in our library10.1002/jlcr.3519
981.
Altomonte S.; Telu S.; Lu S.; Pike V. W. Pd(0)-Mediated 11C-Carbonylation of Aryl(mesityl)iodonium Salts as a Route to [11C]Arylcarboxylic Acids and Derivatives. J. Org. Chem. 2017, 82, 11925–11932..
Not in our library10.1021/acs.joc.7b01704
982.
Hong F.; Lu N.; Lu B.; Cheng J. Synthesis of Fused Heterocycles via One-pot Oxidative O-Arylation, Pd-Catalyzed C(sp3)-H Arylation. Adv. Synth. Catal. 2017, 359, 3299–3303..
Not in our library10.1002/adsc.201700761
983.
Wang Y.; Zhang Y.; Wang L.; Han J. Late-stage Modification of Coumarins via Aryliodonium Intramolecular Aryl Migration. Asian J. Org. Chem. 2022, 11, e202100669.
Not in our library10.1002/ajoc.202100669
984.
Linde E.; Olofsson B. Synthesis of Complex Diarylamines through a Ring-Opening Difunctionalization Strategy**. Angew. Chem., Int. Ed. 2023, 62, e202310921.
Not in our library10.1002/anie.202310921
985.
Linde E.; Bulfield D.; Kervefors G.; Purkait N.; Olofsson B. Diarylation of N- and O-Nucleophiles through a Metal-Free Cascade Reaction. Chem. 2022, 8, 850–865..
Not in our library10.1016/j.chempr.2022.01.009
986.
Kitamura T.; Gondo K.; Oyamada J. Hypervalent Iodine/Triflate Hybrid Benzdiyne Equivalents: Access to Controlled Synthesis of Polycyclic Aromatic Compounds. J. Am. Chem. Soc. 2017, 139, 8416–8419..
Not in our library10.1021/jacs.7b04483
987.
Yuan H.; Yin W.; Hu J.; Li Y. 3-Sulfonyloxyaryl(Mesityl)Iodonium Triflates as 1,2-Benzdiyne Precursors with Activation via ortho-Deprotonative Elimination Strategy. Nat. Commun. 2023, 14, 1841.
Not in our library10.1038/s41467-023-37196-3
988.
Sundalam S. K.; Nilova A.; Seidl T. L.; Stuart D. R. A Selective C-H Deprotonation Strategy to Access Functionalized Arynes by Using Hypervalent Iodine. Angew. Chem., Int. Ed. 2016, 55, 8431–8434..
Not in our library10.1002/anie.201603222
989.
Nilova A.; Metze B.; Stuart D. R. Aryl(TMP)iodonium Tosylate Reagents as a Strategic Entry Point to Diverse Aryl Intermediates: Selective Access to Arynes. Org. Lett. 2021, 23, 4813–4817..
Not in our library10.1021/acs.orglett.1c01534
990.
Yoshimura A.; Ngo K.; Mironova I. A.; Gardner Z. S.; Rohde G. T.; Ogura N.; Ueki A.; Yusubov M. S.; Saito A.; Zhdankin V. V. Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides. Org. Lett. 2024, 26, 1891–1895..
Not in our library10.1021/acs.orglett.4c00197
991.
Yoshimura A.; Fuchs J. M.; Middleton K. R.; Maskaev A. V.; Rohde G. T.; Saito A.; Postnikov P. S.; Yusubov M. S.; Nemykin V. N.; Zhdankin V. V. Pseudocyclic Arylbenziodoxaboroles: Efficient Benzyne Precursors Triggered by Water at Room Temperature. Chem. - Eur. J. 2017, 23, 16738–16742..
Not in our library10.1002/chem.201704393
992.
Yoshimura A.; Ngo K.; Mironova I. A.; Gardner Z. S.; Ogura N.; Ueki A.; Yusubov M. S.; Saito A.; Zhdankin V. V. Generation of Benzyne from Aryl Benziodoxaborole Triflate under Aqueous Conditions and its Reactions with Alkyl Aryl Sulfides. ARKIVOC 2024, 2024 (i), 202412213.
Not in our library10.24820/ark.5550190.p012.213
993.
Zhdankin V. V. Hypervalent Heterocycles. Adv. Heterocycl. Chem. 2016, 119, 57–79..
Not in our library10.1016/bs.aihch.2015.11.001
994.
Kumar R.; Dohi T.; Zhdankin V. V. Organohypervalent Heterocycles. Chem. Soc. Rev. 2024, 53, 4786–4827..
Not in our library10.1039/d2cs01055k
995.
Yan T.; Zhou B.; Xue X.-S.; Cheng J.-P. Mechanism and Origin of the Unexpected Chemoselectivity in Fluorocyclization of o-Styryl Benzamides with a Hypervalent Fluoroiodane Reagent. J. Org. Chem. 2016, 81, 9006–9011..
Not in our library10.1021/acs.joc.6b01642
996.
Ulmer A.; Brunner C.; Arnold A. M.; Poethig A.; Gulder T. A Fluorination/Aryl Migration/Cyclization Cascade for the Metal-Free Synthesis of Fluoro-Benzoxazepines. Chem. - Eur. J. 2016, 22, 3660–3664..
Not in our library10.1002/chem.201504749
997.
Ilchenko N. O.; Cortes M. A.; Szabo K. J. Palladium-Catalyzed Iodofluorination of Alkenes Using Fluoro-Iodoxole Reagent. ACS Catal. 2016, 6, 447–450..
Not in our library10.1021/acscatal.5b02022
998.
Cuzzucoli F.; Racicot L.; Valliant J. F.; Murphy G. K. Transition Metal-Free Fluorocyclization of Unsaturated N-Methoxyamides Gives Cyclic N-Methoxyimidates. Tetrahedron 2022, 123, 132982.
Not in our library10.1016/j.tet.2022.132982
999.
Yang S.; Shi S.; Chen Y.; Ding Z. Synthesis of Dihydroxazines and Fluorinated Oxazepanes Using a Hypervalent Fluoroiodine Reagent. J. Org. Chem. 2021, 86, 14004–14010..
Not in our library10.1021/acs.joc.1c00159
1000.
Riley W.; Jones A. C.; Singh K.; Browne D. L.; Stuart A. M. Accessing Novel Fluorinated Heterocycles with the Hypervalent Fluoroiodane Reagent by Solution and Mechanochemical Synthesis. Chem. Commun. 2021, 57, 7406–7409..
Not in our library10.1039/d1cc02587b
1001.
Cortes Gonzalez M. A.; Nordeman P.; Bermejo Gomez A.; Meyer D. N.; Antoni G.; Schou M.; Szabo K. J. [18F]Fluoro-Benziodoxole: a No-Carrier-Added Electrophilic Fluorinating Reagent. Rapid, Simple Radiosynthesis, Purification and Application for Fluorine-18 Labelling. Chem. Commun. 2018, 54, 4286–4289..
Not in our library10.1039/c8cc00526e
1002.
Zhang J.; Szabo K. J.; Himo F. Metathesis Mechanism of Zinc-Catalyzed Fluorination of Alkenes with Hypervalent Fluoroiodine. ACS Catal. 2017, 7, 1093–1100..
Not in our library10.1021/acscatal.6b02731
1003.
Yang B.; Chansaenpak K.; Wu H.; Zhu L.; Wang M.; Li Z.; Lu H. Silver-Promoted (Radio)Fluorination of Unsaturated Carbamates via a Radical Process. Chem. Commun. 2017, 53, 3497–3500..
Not in our library10.1039/c7cc01393k
1004.
Zhou B.; Yan T.; Xue X.-S.; Cheng J.-P. Mechanism of Silver-Mediated Geminal Difluorination of Styrenes with a Fluoroiodane Reagent: Insights into Lewis-Acid-Activation Model. Org. Lett. 2016, 18, 6128–6131..
Not in our library10.1021/acs.orglett.6b03134
1005.
Brunner C.; Andries-Ulmer A.; Kiefl G. M.; Gulder T. Hypervalent Fluoroiodane-Triggered Synthesis of Fluoro-Azabenzoxazepines and Azaindoles. Eur. J. Org. Chem. 2018, 2018, 2615–2621..
Not in our library10.1002/ejoc.201800129
1006.
Zhao P.; Wang W.; Gulder T. Hypervalent Fluoro-iodane-Triggered Semipinacol Rearrangements: Synthesis of α-Fluoro Ketones. Org. Lett. 2023, 25, 6560–6565..
Not in our library10.1021/acs.orglett.3c02384
1007.
Cortes Gonzalez M. A.; Jiang X.; Nordeman P.; Antoni G.; Szabo K. J. Rhodium-Mediated 18F-Oxyfluorination of Diazoketones Using a Fluorine-18-Containing Hypervalent Iodine Reagent. Chem. Commun. 2019, 55, 13358–13361..
Not in our library10.1039/c9cc06905d
1008.
Mai B. K.; Szabo K. J.; Himo F. Mechanisms of Rh-Catalyzed Oxyfluorination and Oxytrifluoromethylation of Diazocarbonyl Compounds with Hypervalent Fluoroiodine. ACS Catal. 2018, 8, 4483–4492..
Not in our library10.1021/acscatal.8b00667
1009.
Yuan W.; Eriksson L.; Szabo K. J. Rhodium-Catalyzed Geminal Oxyfluorination and Oxytrifluoro-Methylation of Diazocarbonyl Compounds. Angew. Chem., Int. Ed. 2016, 55, 8410–8415..
Not in our library10.1002/anie.201602137
1010.
Ren J.; Du F.-H.; Jia M.-C.; Hu Z.-N.; Chen Z.; Zhang C. Ring Expansion Fluorination of Unactivated Cyclopropanes Mediated by a New Monofluoroiodane(III) Reagent. Angew. Chem., Int. Ed. 2021, 60, 24171–24178..
Not in our library10.1002/anie.202108589
1011.
Ilchenko N. O.; Hedberg M.; Szabo K. J. Fluorinative Ring-Opening of Cyclopropanes by Hypervalent Iodine Reagents. An Efficient Method for 1,3-Oxyfluorination and 1,3-Difluorination. Chem. Sci. 2017, 8, 1056–1061..
Not in our library10.1039/c6sc03471c
1012.
Andries-Ulmer A.; Brunner C.; Rehbein J.; Gulder T. Fluorine as a Traceless Directing Group for the Regiodivergent Synthesis of Indoles and Tryptophans. J. Am. Chem. Soc. 2018, 140, 13034–13041..
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1013.
Kiefl G. M.; Gulder T. α-Functionalization of Ketones via a Nitrogen Directed Oxidative Umpolung. J. Am. Chem. Soc. 2020, 142, 20577–20582..
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1014.
Jiang X.; Yang L.; Yang W.; Zhu Y.; Fang L.; Yu C. Controllable Synthesis of 3-Chloro- and 3,3-Dichloro-2-Oxindoles via Hypervalent Iodine-Mediated Chlorooxidation. Org. Biomol. Chem. 2019, 17, 6920–6924..
Not in our library10.1039/c9ob01173k
1015.
Zhao Z.; Murphy G. K. Chlorination of Phenylallene Derivatives with 1-Chloro-1,2-Benziodoxol-3-one: Synthesis of Vicinal-Dichlorides and Chlorodienes. Beilstein J. Org. Chem. 2018, 14, 796–802..
Not in our library10.3762/bjoc.14.67
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Parvathaneni S. P.; Perumgani P. C. Regioselective Chlorination of Aryl C-H bonds with Hypervalent Iodine(III) Reagent 1-Chloro-1,2-benziodoxol-3-one. Asian J. Org. Chem. 2018, 7, 324–327..
Not in our library10.1002/ajoc.201700620
1017.
Wang M.; Zhang Y.; Wang T.; Wang C.; Xue D.; Xiao J. Story of an Age-Old Reagent: An Electrophilic Chlorination of Arenes and Heterocycles by 1-Chloro-1,2-benziodoxol-3-one. Org. Lett. 2016, 18, 1976–1979..
Not in our library10.1021/acs.orglett.6b00547
1018.
Egami H.; Yoneda T.; Uku M.; Ide T.; Kawato Y.; Hamashima Y. Difunctionalization of Alkenes Using 1-Chloro-1,2-benziodoxol-3-(1H)-one. J. Org. Chem. 2016, 81, 4020–4030..
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1019.
Sun M.; Chen J.; Ding Z. Synthesis of Oxazolidines and Dihydroxazines via Cyclization of α-Aminated Ketones. J. Org. Chem. 2023, 88, 10647–10654..
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1020.
Wang Y.; Tang K.; Liu Z.; Ning Y. Disulfonation of Terminal Alkynes for 1,2-Bisulfonylethenes. Chem. Commun. 2020, 56, 13141–13144..
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Poeira D. L.; Macara J.; Faustino H.; Coelho J. A. S.; Gois P. M. P.; Marques M. M. B. Hypervalent Iodine Mediated Sulfonamide Synthesis. Eur. J. Org. Chem. 2019, 2019, 2695–2701..
Not in our library10.1002/ejoc.201900259
1022.
Tiwari V.; Badavath V. N.; Singh A. K.; Kandasamy J. A Highly Efficient TEMPO Mediated Oxidation of Sugar Primary Alcohols into Uronic Acids Using 1-Chloro-1,2-Benziodoxol-3(1H)-One at Room Temperature. Tetrahedron Lett. 2018, 59, 2511–2514..
Not in our library10.1016/j.tetlet.2018.05.021
1023.
Yang Z.; Sun F.; Xu J.; Li Y.; Yang K.; Du Y. Preparation, Structural Identification and Reactivities of Two Benziodazole-type I(III) Reagents. Adv. Synth. Catal. 2023, 365, 2730–2736..
Not in our library10.1002/adsc.202300304
1024.
Rivero A. R.; Fodran P.; Ondrejkova A.; Wallentin C.-J. Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis. Org. Lett. 2020, 22, 8436–8440..
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1025.
Liu M.; Huang H.; Chen Y. Cyclic Iodine Reagents Enable Allylic Alcohols for Alkyl Boronate Addition/Rearrangement by Photoredox Catalysis. Chin. J. Chem. 2018, 36, 1209–1212..
Not in our library10.1002/cjoc.201800461
1026.
Wu S.; Chen Y. Selective C-H Acyloxylation of Sulfides/Disulfides Enabled by Hypervalent Iodine Reagents. Adv. Synth. Catal. 2023, 365, 2690–2696..
Not in our library10.1002/adsc.202300360
1027.
Ito E.; Fukushima T.; Kawakami T.; Murakami K.; Itami K. Catalytic Dehydrogenative C-H Imidation of Arenes Enabled by Photo-generated Hole Donation to Sulfonimide. Chem. 2017, 2, 383–392..
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1028.
Yang X.; Sun T.-Y.; Rao Y. A Preliminary Study of Diastereoselectivity in the PdII-Catalyzed C(sp3)-H Alkoxylation of Cyclic Systems. Chem. - Eur. J. 2016, 22, 3273–3277..
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1029.
Sakakibara Y.; Murakami K.; Itami K. C-H Acyloxylation of Polycyclic Aromatic Hydrocarbons. Org. Lett. 2022, 24, 602–607..
Not in our library10.1021/acs.orglett.1c04030
1030.
Hu X.; Li G.-X.; He G.; Chen G. Minisci C-H Alkylation of N-Heteroarenes with Aliphatic Alcohols via β-Scission of Alkoxy Radical Intermediates. Org. Chem. Front. 2019, 6, 3205–3209..
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1031.
Liu Z.; Pan Y.; Zou P.; Huang H.; Chen Y.; Chen Y. Hypervalent Iodine Reagents Enable C-H Alkynylation with Iminophenylacetic Acids via Alkoxyl Radicals. Org. Lett. 2022, 24, 5951–5956..
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1032.
Zhu X.; Han M.-Y.; Li P.; Wang L. Photoinduced Difunctionalization of 2,3-Dihydrofuran for the Efficient Synthesis of 2,3-Disubstituted Tetrahydrofurans. Org. Chem. Front. 2017, 4, 1640–1646..
Not in our library10.1039/c7qo00242d
1033.
Ji W.; Tan H.; Wang M.; Li P.; Wang L. Photocatalyst-Free Hypervalent Iodine Reagent Catalyzed Decarboxylative Acylarylation of Acrylamides with α-Oxocarboxylic Acids Driven by Visible-Light Irradiation. Chem. Commun. 2016, 52, 1462–1465..
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1034.
Ogbu I. M.; Bassani D. M.; Robert F.; Landais Y. Photocatalyzed Decarboxylation of Oxamic Acids under Near-Infrared Conditions. Chem. Commun. 2022, 58, 8802–8805..
Not in our library10.1039/d2cc03155h
1035.
Wang L.; Wang H.; Wang Y.; Shen M.; Li S. Photocatalyzed Synthesis of Unsymmetrical Ureas via the Oxidative Decarboxylation of Oxamic Acids with PANI-g-C3N4-TiO2 Composite under Visible Light. Tetrahedron Lett. 2020, 61, 151962.
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1036.
Jatoi A. H.; Pawar G. G.; Robert F.; Landais Y. Visible-Light Mediated Carbamoyl Radical Addition to Heteroarenes. Chem. Commun. 2019, 55, 466–469..
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1037.
Pawar G. G.; Robert F.; Grau E.; Cramail H.; Landais Y. Visible-Light Photocatalyzed Oxidative Decarboxylation of Oxamic Acids: a Green Route to Urethanes and Ureas. Chem. Commun. 2018, 54, 9337–9340..
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Li J.; Liu Z.; Wu S.; Chen Y. Acyl Radical Smiles Rearrangement To Construct Hydroxybenzophenones by Photoredox Catalysis. Org. Lett. 2019, 21, 2077–2080..
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1039.
Wang J.; Li G.-X.; He G.; Chen G. Photoredox-Mediated Minisci Alkylation of N-Heteroarenes using Carboxylic Acids and Hypervalent Iodine. Asian J. Org. Chem. 2018, 7, 1307–1310..
Not in our library10.1002/ajoc.201800197
1040.
Yang L.; Li H.; Du Y.; Cheng K.; Qi C. Visible Light-Catalyzed Decarboxylative Alkynylation of Arenediazonium Salts with Alkynyl Carboxylic Acids: Direct Access to Aryl Alkynes by Organic Photoredox Catalysis. Adv. Synth. Catal. 2019, 361, 5030–5041..
Not in our library10.1002/adsc.201900603
1041.
Sakakibara Y.; Ito E.; Fukushima T.; Murakami K.; Itami K. Late-Stage Functionalization of Arylacetic Acids by Photoredox-Catalyzed Decarboxylative Carbon-Heteroatom Bond Formation. Chem. - Eur. J. 2018, 24, 9254–9258..
Not in our library10.1002/chem.201802143
1042.
Sakakibara Y.; Cooper P.; Murakami K.; Itami K. Photoredox-Catalyzed Decarboxylative Oxidation of Arylacetic Acids. Chem. - Asian J. 2018, 13, 2410–2413..
Not in our library10.1002/asia.201800529
1043.
Yang B.; Xu X.-H.; Qing F.-L. Synthesis of Difluoroalkylated Arenes by Hydroaryldifluoromethylation of Alkenes with α,α-Difluoroarylacetic Acids under Photoredox Catalysis. Org. Lett. 2016, 18, 5956–5959..
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Wu L.; Hao Y.; Liu Y.; Wang Q. Visible-Light-Induced Intramolecular sp3 C-H Oxidation of 2-Alkyl-Substituted Benzamides for the Synthesis of Functionalized Iminoisobenzofurans. Chem. Commun. 2019, 55, 13908–13911..
Not in our library10.1039/c9cc07791j
1045.
Wang N.; Gu Q.-S.; Li Z.-L.; Li Z.; Guo Y.-L.; Guo Z.; Liu X.-Y. Direct Photocatalytic Synthesis of Medium-Sized Lactams by C-C Bond Cleavage. Angew. Chem., Int. Ed. 2018, 57, 14225–14229..
Not in our library10.1002/anie.201808890
1046.
Zhang W.-M.; Dai J.-J.; Xu J.; Xu H.-J. Visible-Light-Induced C2 Alkylation of Pyridine N-Oxides. J. Org. Chem. 2017, 82, 2059–2066..
Not in our library10.1021/acs.joc.6b02891
1047.
Photoredox-mediated Minisci C–H alkylation of N-heteroarenes using boronic acids and hypervalent iodine · 2016
Corrected
1048.
Dai J.-J.; Zhang W.-M.; Shu Y.-J.; Sun Y.-Y.; Xu J.; Feng Y.-S.; Xu H.-J. Deboronative Cyanation of Potassium Alkyltrifluoroborates via Photoredox Catalysis. Chem. Commun. 2016, 52, 6793–6796..
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1049.
Long L.; Li X.; Tu M.; Zhang Y.; Qiao L.; Luo W.; Chen Z. Hypervalent Iodine(III) Promoted C-H/C-H Amination/Annulation Tandem Reactions: Synthesis of Benzimidazoles from Simple Anilines and Aldehydes. Org. Chem. Front. 2023, 10, 473–479..
Not in our library10.1039/d2qo01644c
1050.
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Qiu L.-J.; Liu D.; Zheng K.; Zhang M.-T.; Zhang C. A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent. Front. Chem. 2020, 8, 183.
Not in our library10.3389/fchem.2020.00183
1052.
Zhdankin V. V.; Krasutsky A. P.; Kuehl C. J.; Simonsen A. J.; Woodward J. K.; Mismash B.; Bolz J. T. Preparation, X-ray Crystal Structure, and Chemistry of Stable Azidoiodinanes - Derivatives of Benziodoxole. J. Am. Chem. Soc. 1996, 118, 5192–5197..
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Zhdankin V. V.; Kuehl C. J.; Krasutsky A. P.; Formaneck M. S.; Bolz J. T. Preparation and Chemistry of Stable Azidoiodinanes - 1-Azido-3,3-Bis(Trifluoromethyl)-3-(1H)-1,2-Benziodoxol 1-Azido-1,2-Benziodoxol-3-(1H)-One. Tetrahedron Lett. 1994, 35, 9677–9680..
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1054.
Alazet S.; Preindl J.; Simonet-Davin R.; Nicolai S.; Nanchen A.; Meyer T.; Waser J. Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion. J. Org. Chem. 2018, 83, 12334–12356..
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1055.
Yang X.-G.; Du F.-H.; Li J.-J.; Zhang C. Late-Stage Dehydroxyazidation of Alcohols Promoted by Trifunctional Hypervalent Azido-Iodine(III) Reagents. Chem. - Eur. J. 2022, 28, e202200272.
Not in our library10.1002/chem.202200272
1056.
Matsumoto K.; Nakajima M.; Nemoto T. Determination of the Best Functional and Basis Sets for Optimization of the Structure of Hypervalent Iodines and Calculation of their First and Second Bond Dissociation Enthalpies. J. Phys. Org. Chem. 2019, 32, e3961.
Not in our library10.1002/poc.3961
1057.
Borrel J.; Waser J. Azido-Alkynylation of Alkenes through Radical-Polar Crossover. Chem. Sci. 2023, 14, 9452–9460..
Not in our library10.1039/d3sc03309k
1058.
Li X.; Qi X.; Hou C.; Chen P.; Liu G. Palladium(II)-Catalyzed Enantioselective Azidation of Unactivated Alkenes. Angew. Chem., Int. Ed. 2020, 59, 17239–17244..
Not in our library10.1002/anie.202006757
1059.
Li H.; Shen S.-J.; Zhu C.-L.; Xu H. Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins. J. Am. Chem. Soc. 2019, 141, 9415–9421..
Not in our library10.1021/jacs.9b04381
1060.
Shirke R. P.; Ramasastry S. S. V. Organocatalytic β-Azidation of Enones Initiated by an Electron-Donor-Acceptor Complex. Org. Lett. 2017, 19, 5482–5485..
Not in our library10.1021/acs.orglett.7b02861
1061.
Bertho S.; Rey-Rodriguez R.; Colas C.; Retailleau P.; Gillaizeau I. Regio- and Stereoselective Iron-Catalyzed Oxyazidation of Enamides Using a Hypervalent Iodine Reagent. Chem. - Eur. J. 2017, 23, 17674–17677..
Not in our library10.1002/chem.201704499
1062.
Alazet S.; Le Vaillant F.; Nicolai S.; Courant T.; Waser J. Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents. Chem. - Eur. J. 2017, 23, 9501–9504..
Not in our library10.1002/chem.201702599
1063.
Yuan Y.-A.; Lu D.-F.; Chen Y.-R.; Xu H. Iron-Catalyzed Direct Diazidation for a Broad Range of Olefins. Angew. Chem., Int. Ed. 2016, 55, 534–538..
Not in our library10.1002/anie.201507550
1064.
Wang N.; Li L.; Li Z.-L.; Yang N.-Y.; Guo Z.; Zhang H.-X.; Liu X.-Y. Catalytic Diverse Radical-Mediated 1,2-Cyanofunctionalization of Unactivated Alkenes via Synergistic Remote Cyano Migration and Protected Strategies. Org. Lett. 2016, 18, 6026–6029..
Not in our library10.1021/acs.orglett.6b02960
1065.
Li L.; Li Z.-L.; Wang F.-L.; Guo Z.; Cheng Y.-F.; Wang N.; Dong X.-W.; Fang C.; Liu J.; Hou C.; Tan B.; Liu X.-Y. Radical Aryl Migration Enables Diversity-Oriented Synthesis of Structurally Diverse Medium/Macro- or Bridged-Rings. Nat. Commun. 2016, 7, 13852.
Not in our library10.1038/ncomms13852
1066.
Lin C.-Z.; Jiang L.-F.; Zhang G.-Y.; Zhou F.-S.; Wu S.-H.; Cao J.; Deng Q.-H. Enantioselective Synthesis of 3a-Azido-Pyrroloindolines by Copper-Catalyzed Asymmetric Dearomative Azidation of Tryptamines. Chem. Commun. 2023, 59, 7831–7834..
Not in our library10.1039/d3cc01438j
1067.
Zheng L.; Wang Z.; Li C.; Wu Y.; Liu Z.; Ning Y. The Azidosulfonylation of Terminal Alkynes Leading to β-Azidovinyl Sulfones. Chem. Commun. 2021, 57, 9874–9877..
Not in our library10.1039/d1cc04268h
1068.
Cong F.; Wei Y.; Tang P. Combining Photoredox and Silver Catalysis for Azidotrifluoromethoxylation of Styrenes. Chem. Commun. 2018, 54, 4473–4476..
Not in our library10.1039/c8cc01096j
1069.
Yanagisawa A.; Takagi K.; Horiguchi M.; Dezaki K.; Marui T.; Saito E.; Ebihara T.; Russell G. M.; Watanabe T.; Midorikawa K. Asymmetric α-Azidation Reaction of β-Ketoesters Catalyzed by Chiral Tin Alkoxides. Asian J. Org. Chem. 2023, 12, e202300213.
Not in our library10.1002/ajoc.202300213
1070.
Ji A. Y.; Thirupathi A.; Hwang J. Y.; Kim Y.; Han G.; Ahn K.-H.; Kang K.; Kang E. J. Iron Catalysis of C(sp3)-H Azidation Using a Heteroarene Radical Cation Strategy. Org. Lett. 2023, 25, 1541–1546..
Not in our library10.1021/acs.orglett.3c00330
1071.
He C.; Wu Z.; Zhou Y.; Cao W.; Feng X. Asymmetric Catalytic Nitrooxylation and Azidation of β-Keto Amides/Esters with Hypervalent Iodine Reagents. Org. Chem. Front. 2022, 9, 703–708..
Not in our library10.1039/d1qo01634b
1072.
Allouche E. M. D.; Simonet-Davin R.; Waser J. N-Terminal Selective C-H Azidation of Proline-Containing Peptides: a Platform for Late-Stage Diversification. Chem. - Eur. J. 2022, 28, e202200368.
Not in our library10.1002/chem.202200368
1073.
Wang C.-J.; Sun J.; Zhou W.; Xue J.; Ren B.-T.; Zhang G.-Y.; Mei Y.-L.; Deng Q.-H. Enantioselective Copper-Catalyzed Electrophilic Dearomative Azidation of β-Naphthols. Org. Lett. 2019, 21, 7315–7319..
Not in our library10.1021/acs.orglett.9b02604
1074.
Wang Y.; Hu X.; Morales-Rivera C. A.; Li G.-X.; Huang X.; He G.; Liu P.; Chen G. Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds. J. Am. Chem. Soc. 2018, 140, 9678–9684..
Not in our library10.1021/jacs.8b05753
1075.
Wang Y.; Fang Z.; Chen X.; Wang Y. Mild Dirhodium(II)-Catalyzed Chemo- and Regioselective Azidation of Arenes. Org. Lett. 2018, 20, 5732–5736..
Not in our library10.1021/acs.orglett.8b02446
1076.
Hendrick C. E.; Bitting K. J.; Cho S.; Wang Q. Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation. J. Am. Chem. Soc. 2017, 139, 11622–11628..
Not in our library10.1021/jacs.7b07661
1077.
Rabet P. T. G.; Fumagalli G.; Boyd S.; Greaney M. F. Benzylic C-H Azidation Using the Zhdankin Reagent and a Copper Photoredox Catalyst. Org. Lett. 2016, 18, 1646–1649..
Not in our library10.1021/acs.orglett.6b00512
1078.
Karimov R. R.; Sharma A.; Hartwig J. F. Late Stage Azidation of Complex Molecules. ACS Cent. Sci. 2016, 2, 715–724..
Not in our library10.1021/acscentsci.6b00214
1079.
Nakajima M.; Nagasawa S.; Matsumoto K.; Kuribara T.; Muranaka A.; Uchiyama M.; Nemoto T. A Direct S0→Tn Transition in the Photoreaction of Heavy-Atom-Containing Molecules. Angew. Chem., Int. Ed. 2020, 59, 6847–6852..
Not in our library10.1002/anie.201915181
1080.
Tiffner M.; Stockhammer L.; Schoergenhumer J.; Roeser K.; Waser M. Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters. Molecules 2018, 23, 1142.
Not in our library10.3390/molecules23051142
1081.
Day C. S.; Fawcett A.; Chatterjee R.; Hartwig J. F. Mechanistic Investigation of the Iron-Catalyzed Azidation of Alkyl C(sp3)–H Bonds with Zhdankin’s λ3-Azidoiodane. J. Am. Chem. Soc. 2021, 143, 16184–16196..
Not in our library10.1021/jacs.1c07330
1082.
Huang L.; Xun X.; Zhao M.; Xue J.; Li G.; Hong L. Copper-Catalyzed Regioselective sp3 C-H Azidation of Alkyl Substituents of Indoles and Tetrahydrocarbazoles. J. Org. Chem. 2019, 84, 11885–11890..
Not in our library10.1021/acs.joc.9b01742
1083.
Wang Y.; He Q.; Cao Z.; Wang P.; Chen G.; Beller M. Hypervalent-Iodine Promoted Selective Cleavage of C(sp3)-C(sp3) Bonds in Ethers. Org. Chem. Front. 2022, 9, 5592–5598..
Not in our library10.1039/d2qo01114j
1084.
Wang Y.; Wang N.; Zhao J.; Sun M.; You H.; Fang F.; Liu Z.-Q. Visible-Light-Promoted Site-Specific and Diverse Functionalization of a C(sp3)-C(sp3) Bond Adjacent to an Arene. ACS Catal. 2020, 10, 6603–6612..
Not in our library10.1021/acscatal.0c01495
1085.
He Q.; Cao Z.; Zhang Y.; Chen G.; Wang Y. Visible-Light-Promoted Aliphatic C-H Chlorination and Bromination Using Haloform as the Halogen Donor and Azidobenziodoxole as the Mediator. Adv. Synth. Catal. 2023, 365, 2711–2717..
Not in our library10.1002/adsc.202300416
1086.
Ge Y.; Shao Y.; Wu S.; Liu P.; Li J.; Qin H.; Zhang Y.; Xue X.-s.; Chen Y. Distal Amidoketone Synthesis Enabled by Dimethyl Benziodoxoles via Dual Copper/Photoredox Catalysis. ACS Catal. 2023, 13, 3749–3756..
Not in our library10.1021/acscatal.3c00230
1087.
Poeira D. L.; Negrao A. C. R.; Faustino H.; Coelho J. A. S.; Gomes C. S. B.; Gois P. M. P.; Marques M. M. B. Hypervalent Iodine(III) Reagents with Transferable Primary Amines: Structure and Reactivity on the Electrophilic α-Amination of Stabilized Enolates. Org. Lett. 2022, 24, 776–781..
Not in our library10.1021/acs.orglett.1c04312
1088.
Zhang Y.; Lu J.; Lan T.; Cheng S.; Liu W.; Chen C. Preparation, Characterization, and Reactivity of Aliphatic Amino Iodane(III) Reagents. Eur. J. Org. Chem. 2021, 2021, 436–442..
Not in our library10.1002/ejoc.202001373
1089.
Lan T.; Qin H.; Chen W.; Liu W.; Chen C. Synthesis and Reactivity of Carbazole-Containing Hypervalent Iodine(III) Reagents. Chin. Chem. Lett. 2020, 31, 357–360..
Not in our library10.1016/j.cclet.2019.07.031
1090.
Kiyokawa K.; Okumatsu D.; Minakata S. Synthesis of Hypervalent Iodine(III) Reagents Containing a Transferable (Diarylmethylene)amino Group and Their Use in the Oxidative Amination of Silyl Ketene Acetals. Angew. Chem., Int. Ed. 2019, 58, 8907–8911..
Not in our library10.1002/anie.201904971
1091.
Wang H.; Zhang D.; Sheng H.; Bolm C. Sulfoximidoyl-Containing Hypervalent Iodine(III) Reagents: 1-Sulfoximidoyl-1,2-benziodoxoles. J. Org. Chem. 2017, 82, 11854–11858..
Not in our library10.1021/acs.joc.7b01535
1092.
Wang H.; Zhang D.; Bolm C. Photocatalytic Additions of 1-Sulfoximidoyl-1,2-Benziodoxoles to Styrenes. Chem. - Eur. J. 2018, 24, 14942–14945..
Not in our library10.1002/chem.201803975
1093.
Okumatsu D.; Kiyokawa K.; Bao Nguyen L. T.; Abe M.; Minakata S. Photoexcitation of (Diarylmethylene)Amino Benziodoxolones for Alkylamination of Styrene Derivatives with Carboxylic Acids. Chem. Sci. 2024, 15, 1068–1076..
Not in our library10.1039/d3sc06090j
1094.
Okumatsu D.; Kawanaka K.; Kainuma S.; Kiyokawa K.; Minakata S. α-Amination of Carbonyl Compounds by Using Hypervalent Iodine-Based Aminating Reagents Containing a Transferable (Diarylmethylene)amino Group. Chem. - Eur. J. 2023, 29, e202203722.
Not in our library10.1002/chem.202203722
1095.
Chen J.-Y.; Huang J.; Sun K.; He W.-M. Recent Advances in Transition-Metal-Free Trifluoromethylation with Togni’s Reagents. Org. Chem. Front. 2022, 9, 1152–1164..
Not in our library10.1039/d1qo01504d
1096.
Charpentier J.; Fruh N.; Togni A. Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents. Chem. Rev. 2015, 115, 650–682..
Not in our library10.1021/cr500223h
1097.
Matousek V.; Vaclavik J.; Hajek P.; Charpentier J.; Blastik Z. E.; Pietrasiak E.; Budinska A.; Togni A.; Beier P. Expanding the Scope of Hypervalent Iodine Reagents for Perfluoroalkylation: From Trifluoromethyl to Functionalized Perfluoroethyl. Chem. - Eur. J. 2016, 22, 417–424..
Not in our library10.1002/chem.201503531
1098.
Zhu J.; Li Y.; Ni C.; Shen Q. Pentafluoroethylbenziodoxole (BIX-C2F5): a Shelf-Stable Reagent for Pentafluoroethylation of β-Ketoesters and Arylboronic Acids. Chin. J. Chem. 2016, 34, 662–668..
Not in our library10.1002/cjoc.201600097
1099.
Liebing P.; Pietrasiak E.; Otth E.; Kalim J.; Bornemann D.; Togni A. Supramolecular Aggregation of Perfluoroorganyl Iodane Reagents in the Solid State and in Solution. Eur. J. Org. Chem. 2018, 2018, 3771–3781..
Not in our library10.1002/ejoc.201800358
1100.
Kalim J.; Duhail T.; Le T.-N.; Vanthuyne N.; Anselmi E.; Togni A.; Magnier E. Merging Hypervalent Iodine and Sulfoximine Chemistry: a New Electrophilic Trifluoromethylation Reagent. Chem. Sci. 2019, 10, 10516–10523..
Not in our library10.1039/c9sc04289j
1101.
Liebing P.; Kalim J.; Arefyeva N.; Oehler F.; Wickleder M.; Togni A. A Tunable Trifluoromethyliodonium Reagent. Angew. Chem., Int. Ed. 2019, 58, 8585–8588..
Not in our library10.1002/anie.201903623
1102.
Liang A.; Han S.; Liu Z.; Wang L.; Li J.; Zou D.; Wu Y.; Wu Y. Regioselective Synthesis of N-Heteroaromatic Trifluoromethoxy Compounds by Direct O-CF3 Bond Formation. Chem. - Eur. J. 2016, 22, 5102–5106..
Not in our library10.1002/chem.201505181
1103.
Vaclavik J.; Zschoche R.; Klimankova I.; Matousek V.; Beier P.; Hilvert D.; Togni A. Irreversible Cysteine-Selective Protein Labeling Employing Modular Electrophilic Tetrafluoroethylation Reagents. Chem. - Eur. J. 2017, 23, 6490–6494..
Not in our library10.1002/chem.201700607
1104.
Kalim J.; Duhail T.; Pietrasiak E.; Anselmi E.; Magnier E.; Togni A. Direct Trifluoromethylation of Alcohols Using a Hypervalent Iodosulfoximine Reagent. Chem. - Eur. J. 2021, 27, 2638–2642..
Not in our library10.1002/chem.202005104
1105.
Scattolin T.; Bortolamiol E.; Visentin F.; Palazzolo S.; Caligiuri I.; Perin T.; Canzonieri V.; Demitri N.; Rizzolio F.; Togni A. Palladium(II)-η3-Allyl Complexes Bearing N-Trifluoromethyl N-Heterocyclic Carbenes: A New Generation of Anticancer Agents that Restrain the Growth of High-Grade Serous Ovarian Cancer Tumoroids. Chem. - Eur. J. 2020, 26, 11868–11876..
Not in our library10.1002/chem.202002199
1106.
Halimehjani A. Z.; Dracinsky M.; Beier P. One-Pot Three-Component Route for the Synthesis of S-Trifluoromethyl Dithiocarbamates Using Togni’s Reagent. Beilstein J. Org. Chem. 2017, 13, 2502–2508..
Not in our library10.3762/bjoc.13.247
1107.
Geri J. B.; Wade Wolfe M. M.; Szymczak N. K. Borazine-CF3- Adducts for Rapid, Room Temperature, and Broad Scope Trifluoromethylation. Angew. Chem., Int. Ed. 2018, 57, 1381–1385..
Not in our library10.1002/anie.201711316
1108.
Abegg D.; Tomanik M.; Qiu N.; Pechalrieu D.; Shuster A.; Commare B.; Togni A.; Herzon S. B.; Adibekian A. Chemoproteomic Profiling by Cysteine Fluoroalkylation Reveals Myrocin G as an Inhibitor of the Nonhomologous End Joining DNA Repair Pathway. J. Am. Chem. Soc. 2021, 143, 20332–20342..
Not in our library10.1021/jacs.1c09724
1109.
Zhao Y.; Wang X.; Yao R.; Li C.; Xu Z.; Zhang L.; Han G.; Hou J.; Liu Y.; Song Y. Iron-Catalyzed Alkene Trifluoromethylation in Tandem with Phenol Dearomatizing Spirocyclization: Regioselective Construction of Trifluoromethylated Spirocarbocycles. Adv. Synth. Catal. 2022, 364, 637–642..
Not in our library10.1002/adsc.202101201
1110.
Yuan S.; Liu X.; Huang Z.; Gui S.; Diao Y.; Peng Y.-Y.; Ding Q. Tetrabutylammonium Chloride-Induced Cascade Radical Addition/Cyclization of O-Isocyanodiaryl Amines: A Novel Protocol for the Synthesis of 11-Trifluoromethylated Dibenzodiazepines. J. Org. Chem. 2022, 87, 16542–16549..
Not in our library10.1021/acs.joc.2c02100
1111.
Xi J.-M.; Sun Y.-H.; Li W.-C.; Wu Y.-H.; Wei Z.-L.; Liao W.-W. Radical Alkene-Trifluoromethylation-Triggered Nitrile Insertion/Remote Functionalization Relay Processes: Diverse Synthesis of Trifluoromethylated Azaheterocycles Enabled by Copper Catalysis. Org. Lett. 2022, 24, 1110–1115..
Not in our library10.1021/acs.orglett.2c00083
1112.
Chen Y.; Wu X.; Yang S.; Zhu C. Asymmetric Radical Cyclization of Alkenes by Stereospecific Homolytic Substitution of Sulfinamides. Angew. Chem., Int. Ed. 2022, 61, e202201027.
Not in our library10.1002/anie.202201027
1113.
Zuo H.-D.; Ji X.-S.; Guo C.; Tu S.-J.; Hao W.-J.; Jiang B. Cu-Catalyzed Radical-Triggered Spirotricyclization of Enediynes and Enyne-Nitriles for the Synthesis of Pentacyclic Spiroindenes. Org. Chem. Front. 2021, 8, 1496–1502..
Not in our library10.1039/d0qo01640c
1114.
Zhou G.; Su J.; Shang T.; Wang X.; Bai Y.; Yuan Z.; Zhu G. Synthesis of Polysubstituted Azetidines via Cascade Trifluoromethylation/Cyclization of N-Allyl Ynamides. Org. Chem. Front. 2021, 8, 4473–4478..
Not in our library10.1039/d1qo00559f
1115.
Zhang Z.-Q.; Xu Y.-H.; Dai J.-C.; Li Y.; Sheng J.; Wang X.-S. Copper-Catalyzed Trifluoromethylation/Cyclization of Alkynes for Synthesis of Dioxodibenzothiazepines. Org. Lett. 2021, 23, 2194–2198..
Not in our library10.1021/acs.orglett.1c00344
1116.
Wang Z.-S.; Chen Y.-B.; Zhang H.-W.; Sun Z.; Zhu C.; Ye L.-W. Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines. J. Am. Chem. Soc. 2020, 142, 3636–3644..
Not in our library10.1021/jacs.9b13975
1117.
Terhorst S.; Tiwari D. P.; Meister D.; Petran B.; Rissanen K.; Bolm C. Syntheses of Trifluoroethylated N-Heterocycles from Vinyl Azides and Togni’s Reagent Involving 1,n-Hydrogen-Atom Transfer Reactions. Org. Lett. 2020, 22, 4766–4770..
Not in our library10.1021/acs.orglett.0c01566
1118.
Mao S.; Wang H.; Liu L.; Wang X.; Zhou M.-D.; Li L. Trifluoromethylation/Difluoromethylation-Initiated Radical Cyclization of o-Alkenyl Aromatic Isocyanides for Direct Construction of 4-Cyano-2-Trifluoromethyl/Difluoromethyl-Containing Quinolines. Adv. Synth. Catal. 2020, 362, 2274–2279..
Not in our library10.1002/adsc.202000155
1119.
Cheng Y.-F.; Liu J.-R.; Gu Q.-S.; Yu Z.-L.; Wang J.; Li Z.-L.; Bian J.-Q.; Wen H.-T.; Wang X.-J.; Hong X.; Liu X.-Y. Catalytic Enantioselective Desymmetrizing Functionalization of Alkyl Radicals via Cu(I)/CPA Cooperative Catalysis. Nat. Catal. 2020, 3, 401–410..
Not in our library10.1038/s41929-020-0439-8
1120.
Mou X.-Q.; Rong F.-M.; Zhang H.; Chen G.; He G. Copper(I)-Catalyzed Enantioselective Intramolecular Aminotrifluoromethylation of O-Homoallyl Benzimidates. Org. Lett. 2019, 21, 4657–4661..
Not in our library10.1021/acs.orglett.9b01552
1121.
Luebbesmeyer M.; Leifert D.; Schaefer H.; Studer A. Electrochemical Initiation of Electron-Catalyzed Phenanthridine Synthesis by Trifluoromethylation of Isonitriles. Chem. Commun. 2018, 54, 2240–2243..
Not in our library10.1039/c7cc09302k
1122.
Li X.-T.; Gu Q.-S.; Dong X.-Y.; Meng X.; Liu X.-Y. A Copper Catalyst with a Cinchona-Alkaloid-Based Sulfonamide Ligand for Asymmetric Radical Oxytrifluoromethylation of Alkenyl Oximes. Angew. Chem., Int. Ed. 2018, 57, 7668–7672..
Not in our library10.1002/anie.201804315
1123.
Wang L.; Studer A. 1-Trifluoromethylisoquinolines from α-Benzylated Tosylmethyl Isocyanide Derivatives in a Modular Approach. Org. Lett. 2017, 19, 5701–5704..
Not in our library10.1021/acs.orglett.7b02882
1124.
Ricci P.; Khotavivattana T.; Pfeifer L.; Medebielle M.; Morphy J. R.; Gouverneur V. The dual role of thiourea in the thiotrifluoromethylation of alkenes. Chem. Sci. 2017, 8, 1195–1199..
Not in our library10.1039/c6sc02790c
1125.
Gorbanev Y.; Leifert D.; Studer A.; O’Connell D.; Chechik V. Initiating Radical Reactions with Non-Thermal Plasmas. Chem. Commun. 2017, 53, 3685–3688..
Not in our library10.1039/c7cc01157a
1126.
Zhu C.-L.; Wang C.; Qin Q.-X.; Yruegas S.; Martin C. D.; Xu H. Iron(II)-Catalyzed Azidotrifluoromethylation of Olefins and N-Heterocycles for Expedient Vicinal Trifluoromethyl Amine Synthesis. ACS Catal. 2018, 8, 5032–5037..
Not in our library10.1021/acscatal.8b01253
1127.
Liu W.; Pu M.; He J.; Zhang T.; Dong S.; Liu X.; Wu Y.-D.; Feng X. Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds. J. Am. Chem. Soc. 2021, 143, 11856–11863..
Not in our library10.1021/jacs.1c05881
1128.
Wang Z.; Cheng J.-T.; Shi Z.; Wang N.; Zhan F.; Jiang S.-P.; Lin J.-S.; Jiang Y.; Liu X.-Y. Catalytic Asymmetric Intermolecular Radical Aminotrifluoromethylation of Alkenes with Hydrazines by Cu(I)/CPA Cooperative Catalysis. ChemCatChem. 2021, 13, 185–190..
Not in our library10.1002/cctc.202001398
1129.
Zheng L.; Cai L.; Zhuo X.; Deng L.; Wu Y.; Yang B.; Wang Y.; Guo W. Direct Intermolecular Three-Component Aminotrifluoromethylation of Styrenes by Visible-Light-Photoredox Catalysis. Org. Chem. Front. 2022, 9, 6498–6504..
Not in our library10.1039/d2qo00985d
1130.
Chen C.-T.; Chen Y.-P.; Tsai B.-Y.; Liao Y.-Y.; Su Y.-C.; Chen T.-C.; Lu C.-H.; Fujii R.; Kawashima K.; Mori S. Vanadyl Species-Catalyzed 1,2-Oxidative Trifluoromethylation of Unactivated Olefins. ACS Catal. 2020, 10, 3676–3683..
Not in our library10.1021/acscatal.0c00370
1131.
Chen C.-T.; Su Y.-C.; Lu C.-H.; Lien C.-I.; Hung S.-F.; Hsu C.-W.; Agarwal R.; Modala R.; Tseng H.-M.; Tseng P.-X.; Fujii R.; Kawashima K.; Mori S. Enantioselective Radical Type, 1,2-Oxytrifluoromethylation of Olefins Catalyzed by Chiral Vanadyl Complexes: Importance of Noncovalent Interactions. ACS Catal. 2021, 11, 7160–7175..
Not in our library10.1021/acscatal.1c01813
1132.
Zhang G.; Zhou S.; Fu L.; Chen P.; Li Y.; Zou J.; Liu G. Asymmetric Coupling of Carbon-Centered Radicals Adjacent to Nitrogen: Copper-Catalyzed Cyanation and Etherification of Enamides. Angew. Chem., Int. Ed. 2020, 59, 20439–20444..
Not in our library10.1002/anie.202008338
1133.
Wu L.; Wang F.; Wan X.; Wang D.; Chen P.; Liu G. Asymmetric Cu-Catalyzed Intermolecular Trifluoromethylarylation of Styrenes: Enantioselective Arylation of Benzylic Radicals. J. Am. Chem. Soc. 2017, 139, 2904–2907..
Not in our library10.1021/jacs.6b13299
1134.
Zhou S.; Song T.; Chen H.; Liu Z.; Shen H.; Li C. Catalytic Radical Trifluoromethylalkynylation of Unactivated Alkenes. Org. Lett. 2017, 19, 698–701..
Not in our library10.1021/acs.orglett.6b03870
1135.
Fu L.; Zhou S.; Wan X.; Chen P.; Liu G. Enantioselective Trifluoromethylalkynylation of Alkenes via Copper-Catalyzed Radical Relay. J. Am. Chem. Soc. 2018, 140, 10965–10969..
Not in our library10.1021/jacs.8b07436
1136.
Lin J.-S.; Li T.-T.; Liu J.-R.; Jiao G.-Y.; Gu Q.-S.; Cheng J.-T.; Guo Y.-L.; Hong X.; Liu X.-Y. Cu/Chiral Phosphoric Acid-Catalyzed Asymmetric Three-Component Radical-Initiated 1,2-Dicarbofunctionalization of Alkenes. J. Am. Chem. Soc. 2019, 141, 1074–1083..
Not in our library10.1021/jacs.8b11736
1137.
Wu L.; Wang F.; Chen P.; Liu G. Enantioselective Construction of Quaternary All-Carbon Centers via Copper-Catalyzed Arylation of Tertiary Carbon-Centered Radicals. J. Am. Chem. Soc. 2019, 141, 1887–1892..
Not in our library10.1021/jacs.8b13052
1138.
Li J.-L.; Liu Y.-Q.; Zou W.-L.; Zeng R.; Zhang X.; Liu Y.; Han B.; He Y.; Leng H.-J.; Li Q.-Z. Radical Acylfluoroalkylation of Olefins through N-Heterocyclic Carbene Organocatalysis. Angew. Chem., Int. Ed. 2020, 59, 1863–1870..
Not in our library10.1002/anie.201912450
1139.
Zhang B.; Peng Q.; Guo D.; Wang J. NHC-Catalyzed Radical Trifluoromethylation Enabled by Togni Reagent. Org. Lett. 2020, 22, 443–447..
Not in our library10.1021/acs.orglett.9b04203
1140.
Zhou S.; Zhang G.; Fu L.; Chen P.; Li Y.; Liu G. Copper-Catalyzed Asymmetric Cyanation of Alkenes via Carbonyl-Assisted Coupling of Alkyl-Substituted Carbon-Centered Radicals. Org. Lett. 2020, 22, 6299–6303..
Not in our library10.1021/acs.orglett.0c02085
1141.
Wang M.; Wang Q.; Ma M.; Zhao B. Copper-Catalysed Synthesis of Trifluoromethyl Allenes via Fluoro-Carboalkynylation of Alkenes. Org. Chem. Front. 2022, 9, 1844–1849..
Not in our library10.1039/d1qo01823j
1142.
Liu Y.-Q.; Li Q.-Z.; Kou X.-X.; Zeng R.; Qi T.; Zhang X.; Peng C.; Han B.; Li J.-L. Radical Acylalkylation of 1,3-Enynes to Access Allenic Ketones via N-Heterocyclic Carbene Organocatalysis. J. Org. Chem. 2022, 87, 5229–5241..
Not in our library10.1021/acs.joc.2c00037
1143.
Liang H.; Ji D.-S.; Xu G.-Q.; Luo Y.-C.; Zheng H.; Xu P.-F. Metal-Free, Visible-Light Induced Enantioselective Three-Component Dicarbofunctionalization and Oxytrifluoromethylation of Enamines via Chiral Phosphoric Acid Catalysis. Chem. Sci. 2022, 13, 1088–1094..
Not in our library10.1039/d1sc06613g
1144.
Yuan Q.; Huang Z.; Chai Z.; Hong D.; Zhu S.; Zhou S.; Zhu X.; Wei Y.; Wang S. Indolyl-based Copper(I) Complex-Catalyzed Intermolecular Trifluoromethylazolation of Alkenes via Radical Process. Org. Lett. 2022, 24, 8948–8953..
Not in our library10.1021/acs.orglett.2c03370
1145.
Fu L.; Chen X.; Fan W.; Chen P.; Liu G. Copper-Catalyzed Asymmetric Functionalization of Vinyl Radicals for the Access to Vinylarene Atropisomers. J. Am. Chem. Soc. 2023, 145, 13476–13483..
Not in our library10.1021/jacs.3c04498
1146.
Tang H.; Kuang Y.; Zeng J.; Li X.; Zhou W.; Lu Y. Combinatorial Synthesis and Biological Evaluations of (E)-β-Trifluoromethyl Vinylsulfones as Antitumor Agents. RSC Adv. 2019, 9, 31474–31482..
Not in our library10.1039/c9ra06368d
1147.
Xiang Y.; Li Y.; Kuang Y.; Wu J. Stereoselective Vicinal Difunctionalization of Alkynes through a Three-Component Reaction of Alkynes, Sodium Sulfinates, and Togni Reagent. Adv. Synth. Catal. 2017, 359, 2605–2609..
Not in our library10.1002/adsc.201700278
1148.
Xu P.; Fan W.; Chen P.; Liu G. Enantioselective Radical Trifluoromethylation of Benzylic C-H Bonds via Cooperative Photoredox and Copper Catalysis. J. Am. Chem. Soc. 2022, 144, 13468–13474..
Not in our library10.1021/jacs.2c06432
1149.
Winter M.; Schuetz R.; Eitzinger A.; Ofial A. R.; Waser M. CF3-Containing para-Quinone Methides for Organic Synthesis. Eur. J. Org. Chem. 2020, 2020, 3812–3817..
Not in our library10.1002/ejoc.202000295
1150.
Sarver P. J.; Bacauanu V.; Schultz D. M.; Di Rocco D. A.; Lam Y.-h.; Sherer E. C.; MacMillan D. W. C. The Merger of Decatungstate and Copper Catalysis to Enable Aliphatic C(sp3)-H Trifluoromethylation. Nat. Chem. 2020, 12, 459–467..
Not in our library10.1038/s41557-020-0436-1
1151.
Feng P.; Lee K. N.; Lee J. W.; Zhan C.; Ngai M.-Y. Access to a New Class of Synthetic Building Blocks via Trifluoromethoxylation of Pyridines and Pyrimidines. Chem. Sci. 2016, 7, 424–429..
Not in our library10.1039/c5sc02983j
1152.
Gao G.-L.; Yang C.; Xia W. Selective C-H Trifluoromethylation of Benzimidazoles through Photoredox Catalysis. Chem. Commun. 2017, 53, 1041–1044..
Not in our library10.1039/c6cc08975e
1153.
Xie Z.; Luo S.; Zhu Q. Pd-Catalyzed C(sp2)-H Carbonylation of 2-Benzylpyridines for the Synthesis of Pyridoisoquinolinones. Chem. Commun. 2016, 52, 12873–12876..
Not in our library10.1039/c6cc07612b
1154.
Gao X.; Geng Y.; Han S.; Liang A.; Li J.; Zou D.; Wu Y.; Wu Y. Nickel-Catalyzed Direct C-H Trifluoromethylation of Free Anilines with Togni’s Reagent. Org. Lett. 2018, 20, 3732–3735..
Not in our library10.1021/acs.orglett.8b01216
1155.
Frederic C. J. M.; Cornil J.; Vandamme M.; Dumitrescu L.; Tikad A.; Robiette R.; Vincent S. P. Highly (Z)-Diastereoselective Synthesis of Trifluoromethylated exo-Glycals via Photoredox and Copper Catalysis. Org. Lett. 2018, 20, 6769–6773..
Not in our library10.1021/acs.orglett.8b02891
1156.
Shi Y.; Wang K.; Ding Y.; Xie Y. Transition-Metal-Free Electrochemical Oxidative C(sp2)-H Trifluoromethylation of Aryl Aldehyde Hydrazones. Org. Biomol. Chem. 2022, 20, 9362–9367..
Not in our library10.1039/d2ob01734b
1157.
Deolka S.; Govindarajan R.; Vasylevskyi S.; Roy M. C.; Khusnutdinova J. R.; Khaskin E. Ligand-Free Nickel Catalyzed Perfluoroalkylation of Arenes and Heteroarenes. Chem. Sci. 2022, 13, 12971–12979..
Not in our library10.1039/d2sc03879j
1158.
Chen X.; Ding L.; Li L.; Li J.; Zou D.; Wu Y.; Wu Y. Transition Metal-Free Direct C-H Trifluoromethyltion of (Hetero)Arenes with Togni’s Reagent. Tetrahedron Lett. 2020, 61, 151538.
Not in our library10.1016/j.tetlet.2019.151538
1159.
Rahimidashaghoul K.; Klimankova I.; Hubalek M.; Korecky M.; Chvojka M.; Pokorny D.; Matousek V.; Fojtik L.; Kavan D.; Kukacka Z.; Novak P.; Beier P. Reductant-Induced Free Radical Fluoroalkylation of Nitrogen Heterocycles and Innate Aromatic Amino Acid Residues in Peptides and Proteins. Chem. - Eur. J. 2019, 25, 15779–15785..
Not in our library10.1002/chem.201902944
1160.
Zhang Y.; Lee T. S.; Favale J. M.; Leary D. C.; Petersen J. L.; Scholes G. D.; Castellano F. N.; Milsmann C. Delayed Fluorescence from a Zirconium(IV) Photosensitizer with Ligand-to-Metal Charge-Transfer Excited States. Nat. Chem. 2020, 12, 345–352..
Not in our library10.1038/s41557-020-0430-7
1161.
Hang Z.; Tong X.; Li Z.; Wang Z.-y.; Xue W. A Practical Method for N-Cyanation of Secondary Amines and Sulfonamides. Tetrahedron Lett. 2022, 88, 153564.
Not in our library10.1016/j.tetlet.2021.153564
1162.
Chen Z.; Yuan W. N-Cyanation of Primary and Secondary Amines with Cyanobenziodoxolone (CBX) Reagent. Chem. - Eur. J. 2021, 27, 14836–14840..
Not in our library10.1002/chem.202102354
1163.
Maity A.; Roy A.; Das M. K.; De S.; Naskar M.; Bisai A. Oxidative Cyanation of 2-Oxindoles: Formal Total Synthesis of (±)-Gliocladin C. Org. Biomol. Chem. 2020, 18, 1679–1684..
Not in our library10.1039/c9ob02752a
1164.
Ma B.; Lin X.; Lin L.; Feng X.; Liu X. Chiral N,N’-Dioxide Organocatalyzed Asymmetric Electrophilic α-Cyanation of β-Keto Esters and β-Keto Amides. J. Org. Chem. 2017, 82, 701–708..
Not in our library10.1021/acs.joc.6b02726
1165.
Amos S. G. E.; Le Vaillant F.; Waser J. Exploring Photoredox-Catalyzed (Re)functionalizations with Core-Modified Benziodoxolones. Helv. Chim. Acta 2023, 106, e202200161.
Not in our library10.1002/hlca.202200161
1166.
Kong X.; Chen X.; Chen Y.; Cao Z.-Y. Scalable Electrocatalytic Intermolecular Acylcyanation and Aminocyanation of Alkenes. J. Org. Chem. 2022, 87, 7013–7021..
Not in our library10.1021/acs.joc.1c03134
1167.
Declas N.; Le Vaillant F.; Waser J. Revisiting the Urech Synthesis of Hydantoins: Direct Access to Enantiopure 1,5-Substituted Hydantoins Using Cyanobenziodoxolone. Org. Lett. 2019, 21, 524–528..
Not in our library10.1021/acs.orglett.8b03843
1168.
Le Vaillant F.; Wodrich M. D.; Waser J. Room Temperature Decarboxylative Cyanation of Carboxylic Acids Using Photoredox Catalysis and Cyanobenziodoxolones: a Divergent Mechanism Compared to Alkynylation. Chem. Sci. 2017, 8, 1790–1800..
Not in our library10.1039/c6sc04907a
1169.
Cheng H.-C.; Ma J.-L.; Guo P.-H. Cyclic Diaryliodonium Salts: Eco-Friendly and Versatile Building Blocks for Organic Synthesis. Adv. Synth. Catal. 2023, 365, 1112–1139..
Not in our library10.1002/adsc.202201326
1170.
Yang Y.; Xie R.; Wang Y.; Zhu P.; Wang J.; Li S. Efficient Synthesis of Benzo[c]cinnolines and Azoarenes via Dual C-N Coupling of Phthalhydrazide and Trivalent Halogen Reagents. Org. Chem. Front. 2023, 10, 2701–2707..
Not in our library10.1039/d3qo00391d
1171.
Lopez-Lopez J.-C.; Bautista D.; Gonzalez-Herrero P. Phosphorescent Biaryl Platinum(II) Complexes Obtained through Double Metalation of Dibenzoiodolium Ions. Chem. Commun. 2022, 58, 4532–4535..
Not in our library10.1039/d2cc01018f
1172.
Jiang M.; Guo J.; Liu B.; Tan Q.; Xu B. Synthesis of Tellurium-Containing π-Extended Aromatics with Room-Temperature Phosphorescence. Org. Lett. 2019, 21, 8328–8333..
Not in our library10.1021/acs.orglett.9b03106
1173.
Zhu D.; Wu Z.; Luo B.; Du Y.; Liu P.; Chen Y.; Hu Y.; Huang P.; Wen S. Heterocyclic Iodoniums for the Assembly of Oxygen-Bridged Polycyclic Heteroarenes with Water as the Oxygen Source. Org. Lett. 2018, 20, 4815–4818..
Not in our library10.1021/acs.orglett.8b01969
1174.
Wang M.; Fan Q.; Jiang X. Nitrogen-Iodine Exchange of Diaryliodonium Salts: Access to Acridine and Carbazole. Org. Lett. 2018, 20, 216–219..
Not in our library10.1021/acs.orglett.7b03564
1175.
Synthesis of Dibenzofurans from Cyclic Diaryliodonium Triflates and Water via Oxygen–Iodine Exchange Approach · 2018
Not checked
1176.
Wang M.; Chen S.; Jiang X. Construction of Functionalized Annulated Sulfone via SO2/I Exchange of Cyclic Diaryliodonium Salts. Org. Lett. 2017, 19, 4916–4919..
Not in our library10.1021/acs.orglett.7b02388
1177.
Tan Q.; Zhou D.; Zhang T.; Liu B.; Xu B. Iodine-Doped Sumanene and its Application for the Synthesis of Chalcogenasumanenes and Silasumanenes. Chem. Commun. 2017, 53, 10279–10282..
Not in our library10.1039/c7cc05885c
1178.
Wang M.; Zhang M.; Luo Y.; Liu Z.; Yang C.; Lan J.; Wu D.; You J. Pd(II)-Catalyzed Regioselective Multiple C-H Arylations of 1-Naphthamides with Cyclic Diaryliodonium Salts: One-Step Access to [4]- and [5]Carbohelicenes. Org. Lett. 2020, 22, 135–139..
Not in our library10.1021/acs.orglett.9b04046
1179.
Lee J. B.; Jeon M. H.; Seo J. K.; von Helden G.; Rohde J.-U.; Zhao B. S.; Seo J.; Hong S. Y. Annulative π-Extension of Unactivated Benzene Derivatives through Nondirected C-H Arylation. Org. Lett. 2019, 21, 7004–7008..
Not in our library10.1021/acs.orglett.9b02583
1180.
Hu T.; Xu K.; Ye Z.; Zhu K.; Wu Y.; Zhang F. Two-in-One Strategy for the Pd(II)-Catalyzed Tandem C-H Arylation/Decarboxylative Annulation Involved with Cyclic Diaryliodonium Salts. Org. Lett. 2019, 21, 7233–7237..
Not in our library10.1021/acs.orglett.9b02429
1181.
Mathew B. P.; Yang H. J.; Kim J.; Lee J. B.; Kim Y.-T.; Lee S.; Lee C. Y.; Choe W.; Myung K.; Park J.-U.; Hong S. Y. An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C-H Bond Activations. Angew. Chem., Int. Ed. 2017, 56, 5007–5011..
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1182.
Lee J. B.; Kim G. H.; Jeon J. H.; Jeong S. Y.; Lee S.; Park J.; Lee D.; Kwon Y.; Seo J. K.; Chun J.-H.; Kang S. J.; Choe W.; Rohde J.-U.; Hong S. Y. Rapid Access to Polycyclic N-Heteroarenes from Unactivated, Simple Azines via a Base-Promoted Minisci-Type Annulation. Nat. Commun. 2022, 13, 2421.
Not in our library10.1038/s41467-022-30086-0
1183.
Liang W.; Yang Y.; Yang M.; Zhang M.; Li C.; Ran Y.; Lan J.; Bin Z.; You J. Dearomatizing [4 + 1] Spiroannulation of Naphthols: Discovery of Thermally Activated Delayed Fluorescent Materials. Angew. Chem., Int. Ed. 2021, 60, 3493–3497..
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1184.
Peng X.; Luo H.; Wu F.; Zhu D.; Ganesan A.; Huang P.; Wen S. Synthesis of Fluorenes with an All-Carbon Quaternary Center via Palladium-Catalyzed Dual Arylation using Cyclic Diaryliodonium Triflates. Adv. Synth. Catal. 2017, 359, 1152–1156..
Not in our library10.1002/adsc.201601260
1185.
Han J.; Xiao B.; Sun T.-Y.; Wang M.; Jin L.; Yu W.; Wang Y.; Fang D.-M.; Zhou Y.; Wu X.-F.; Wu Y.-D.; Liao J. Enantioselective Double Carbonylation Enabled by High-Valent Palladium Catalysis. J. Am. Chem. Soc. 2022, 144, 21800–21807..
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1186.
Cheng F.; Duan D.-S.; Jiang L.-M.; Li B.-S.; Wang J.-X.; Zhou Y.-J.; Jiao H.-Y.; Wu T.; Zhu D.-Y.; Wang S.-H. Copper-Catalyzed Asymmetric Ring-Opening Reaction of Cyclic Diaryliodonium Salts with Imides. Org. Lett. 2022, 24, 1394–1399..
Not in our library10.1021/acs.orglett.2c00247
1187.
Guo W.; Gu J.; Gu Z. Catalytic Asymmetric Synthesis of Atropisomeric Nitrones: Versatile Intermediate for Axially Chiral Biaryls. Org. Lett. 2020, 22, 7622–7628..
Not in our library10.1021/acs.orglett.0c02830
1188.
Zhu K.; Xu K.; Fang Q.; Wang Y.; Tang B.; Zhang F. Enantioselective Synthesis of Axially Chiral Biaryls via Cu-Catalyzed Acyloxylation of Cyclic Diaryliodonium Salts. ACS Catal. 2019, 9, 4951–4957..
Not in our library10.1021/acscatal.9b00695
1189.
Li Q.; Zhang M.; Zhan S.; Gu Z. Copper-Catalyzed Enantioselective Ring-Opening of Cyclic Diaryliodoniums and O-Alkylhydroxylamines. Org. Lett. 2019, 21, 6374–6377..
Not in our library10.1021/acs.orglett.9b02267
1190.
Li B.; Chao Z.; Li C.; Gu Z. Cu-Catalyzed Enantioselective Ring Opening of Cyclic Diaryliodoniums toward the Synthesis of Chiral Diarylmethanes. J. Am. Chem. Soc. 2018, 140, 9400–9403..
Not in our library10.1021/jacs.8b05743
1191.
Liu M.; Jiang H.; Tang J.; Ye Z.; Zhang F.; Wu Y. meta-Selective O-Arylation of Cyclic Diaryliodonium Salts with Phenols via Aryne Intermediates. Org. Lett. 2023, 25, 2777–2781..
Not in our library10.1021/acs.orglett.3c00600
1192.
Jiang H.; Liu M.; Ye Z.; Song Z.; Wu Y.; Zhang F. Metal-Free meta-Halogenation of Cyclic Diaryliodonium Salts via Aryne Intermediates. Org. Chem. Front. 2023, 10, 3856–3860..
Not in our library10.1039/d3qo00570d
1193.
Le Du E.; Ramirez N. P.; Nicolai S.; Scopelliti R.; Fadaei-Tirani F.; Wodrich M. D.; Hari D. P.; Waser J. X-Ray and NMR Structural Data of Ethynylbenziodoxolones (EBXs) Reagents and Their Analogues. Helv. Chim. Acta 2023, 106, e202200175.
Not in our library10.1002/hlca.202200175
1194.
Kuczmera T. J.; Boelke A.; Nachtsheim B. J. Stabilization of Ethynyl-Substituted Aryl-λ3-Iodanes by Tethered N-Heterocycles. Eur. J. Org. Chem. 2022, 2022, e202200276.
Not in our library10.1002/ejoc.202200276
1195.
Borrel J.; Waser J. Tosyloxybenziodoxolone: A Platform for Performing the Umpolung of Alkynes in One-Pot Transformations. Org. Lett. 2022, 24, 142–146..
Not in our library10.1021/acs.orglett.1c03771
1196.
Le Du E.; Duhail T.; Wodrich M. D.; Scopelliti R.; Fadaei-Tirani F.; Anselmi E.; Magnier E.; Waser J. Structure and Reactivity of N-Heterocyclic Alkynyl Hypervalent Iodine Reagents. Chem. - Eur. J. 2021, 27, 10979–10986..
Not in our library10.1002/chem.202101475
1197.
Ceballos J.; Grinhagena E.; Sangouard G.; Heinis C.; Waser J. Cys-Cys and Cys-Lys Stapling of Unprotected Peptides Enabled by Hypervalent Iodine Reagents. Angew. Chem., Int. Ed. 2021, 60, 9022–9031..
Not in our library10.1002/anie.202014511
1198.
Hari D. P.; Schouwey L.; Barber V.; Scopelliti R.; Fadaei-Tirani F.; Waser J. Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds. Chem. - Eur. J. 2019, 25, 9522–9528..
Not in our library10.1002/chem.201900950
1199.
Le Vaillant F.; Waser J. Alkynylation of Radicals: Spotlight on the ″Third Way″ to Transfer Triple Bonds. Chem. Sci. 2019, 10, 8909–8923..
Not in our library10.1039/c9sc03033f
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Le Vaillant F.; Waser J. Decarboxylative Alkynylation and Cyanation of Carboxylic Acids Using Photoredox Catalysis and Hypervalent Iodine Reagents. Chimia 2017, 71, 226–230..
Not in our library10.2533/chimia.2017.226
1201.
Hou C.; Chen P.; Liu G. Palladium(II)-Catalyzed Markovnikov Hydroalkynylation of Unactivated Terminal Alkenes. Chin. J. Chem. 2024, 42, 29–34..
Not in our library10.1002/cjoc.202300472
1202.
Huang J.; Chen L.-L.; Chen Z.-M. Palladium-Catalyzed Three-Component Cross-Coupling of Conjugated Dienes with Indoles Using Ethynylbenziodazolones as Electrophilic Alkynylating Reagents. Org. Lett. 2022, 24, 5777–5781..
Not in our library10.1021/acs.orglett.2c02275
1203.
Amos S. G. E.; Nicolai S.; Waser J. Photocatalytic Umpolung of N- and O-Substituted Alkenes for the Synthesis of 1,2-Amino Alcohols and Diols. Chem. Sci. 2020, 11, 11274–11279..
Not in our library10.1039/d0sc03655b
1204.
Yang X.; Tsui G. C. Silver-Catalyzed Trifluoromethylalkynylation of Unactivated Alkenes with Hypervalent Iodine Reagents. Org. Lett. 2019, 21, 8625–8629..
Not in our library10.1021/acs.orglett.9b03230
1205.
Li X.; Chen P.; Liu G. Palladium-Catalyzed Intermolecular Alkynylcarbonylation of Unactivated Alkenes: Easy Access to β-Alkynylcarboxylic Esters. Chem. Commun. 2022, 58, 2544–2547..
Not in our library10.1039/d1cc07092d
1206.
Liu Y.; Han C.; Shi H.; Mackenroth A. V.; Zhang L.; Rudolph M.; Rominger F.; Hashmi A. S. K. Gold-Catalyzed Regio- and Stereoselective α-Acyloxy-β-Alkynylation of Ynol Ethers. J. Org. Chem. 2023, 88, 2908–2920..
Not in our library10.1021/acs.joc.2c02597
1207.
Liu Y.; Dietl M. C.; Han C.; Rudolph M.; Rominger F.; Kraemer P.; Hashmi A. S. K. Synthesis of Amide Enol 2-Iodobenzoates by the Regio- and Stereoselective Gold-Catalyzed Acyloxyalkynylation of Ynamides with Hypervalent Iodine Reagents. Org. Lett. 2022, 24, 7101–7106..
Not in our library10.1021/acs.orglett.2c02161
1208.
Cao M.; Ren Y.; Zhang R.; Xu H.; Cheng P.; Xu H.; Xu Y.; Li P. Photochemical ″Cut and Sew″ Transformations of Ethynylbenziodoxolone Reagents and Diazo Compounds. Org. Lett. 2023, 25, 6300–6304..
Not in our library10.1021/acs.orglett.3c02141
1209.
Hari D. P.; Waser J. Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds. J. Am. Chem. Soc. 2017, 139, 8420–8423..
Not in our library10.1021/jacs.7b04756
1210.
Hari D. P.; Waser J. Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds with Hypervalent Iodine Reagents. J. Am. Chem. Soc. 2016, 138, 2190–2193..
Not in our library10.1021/jacs.6b00278
1211.
Ramirez N. P.; Pisella G.; Waser J. Cu(I)-Catalyzed gem-Aminoalkynylation of Diazo Compounds: Synthesis of Fluorinated Propargylic Amines. J. Org. Chem. 2021, 86, 10928–10938..
Not in our library10.1021/acs.joc.1c01423
1212.
Pisella G.; Gagnebin A.; Waser J. Three-Component Reaction for the Synthesis of Highly Functionalized Propargyl Ethers. Chem. - Eur. J. 2020, 26, 10199–10204..
Not in our library10.1002/chem.202001317
1213.
Han C.; Tian X.; Zhang H.; Rominger F.; Hashmi A. S. K. Tetrasubstituted 1,3-Enynes by Gold-Catalyzed Direct C(sp2)-H Alkynylation of Acceptor-Substituted Enamines. Org. Lett. 2021, 23, 4764–4768..
Not in our library10.1021/acs.orglett.1c01486
1214.
Han C.; Liu Y.; Tian X.; Rominger F.; Hashmi A. S. K. Dual Gold/Silver Catalysis: Indolizines from 2-Substituted Pyridine Derivatives via a Tandem C(sp(3))-H Alkynylation/Iminoauration. Org. Lett. 2021, 23, 9480–9484..
Not in our library10.1021/acs.orglett.1c03667
1215.
Voutyritsa E.; Garreau M.; Kokotou M. G.; Triandafillidi I.; Waser J.; Kokotos C. G. Photochemical Functionalization of Heterocycles with EBX Reagents: C-H Alkynylation versus Deconstructive Ring Cleavage. Chem. - Eur. J. 2020, 26, 14453–14460..
Not in our library10.1002/chem.202002868
1216.
Matsumoto K.; Nakajima M.; Nemoto T. Visible Light-Induced Direct S0 → Tn Transition of Benzophenone Promotes C(sp3)-H Alkynylation of Ethers and Amides. J. Org. Chem. 2020, 85, 11802–11811..
Not in our library10.1021/acs.joc.0c01573
1217.
Yang Y.; Antoni P.; Zimmer M.; Sekine K.; Mulks F. F.; Hu L.; Zhang L.; Rudolph M.; Rominger F.; Hashmi A. S. K. Dual Gold/Silver Catalysis Involving Alkynylgold(III) Intermediates Formed by Oxidative Addition and Silver-Catalyzed C-H Activation for the Direct Alkynylation of Cyclopropenes. Angew. Chem., Int. Ed. 2019, 58, 5129–5133..
Not in our library10.1002/anie.201812577
1218.
Kona C. N.; Nishii Y.; Miura M. Iridium-Catalyzed Direct C4- and C7-Selective Alkynylation of Indoles Using Sulfur-Directing Groups. Angew. Chem., Int. Ed. 2019, 58, 9856–9860..
Not in our library10.1002/anie.201904709
1219.
Hermann G. N.; Unruh M. T.; Jung S.-H.; Krings M.; Bolm C. Mechanochemical Rhodium(III)- and Gold(I)-Catalyzed C-H Bond Alkynylations of Indoles under Solventless Conditions in Mixer Mills. Angew. Chem., Int. Ed. 2018, 57, 10723–10727..
Not in our library10.1002/anie.201805778
1220.
Caspers L. D.; Finkbeiner P.; Nachtsheim B. J. Direct Electrophilic C-H Alkynylation of Unprotected 2-Vinylanilines. Chem. - Eur. J. 2017, 23, 2748–2752..
Not in our library10.1002/chem.201606026
1221.
Banerjee S.; Patil N. T. Exploiting the Dual Role of Ethynylbenziodoxolones in Gold-Catalyzed C(sp)-C(sp) Cross-Coupling Reactions. Chem. Commun. 2017, 53, 7937–7940..
Not in our library10.1039/c7cc04283c
1222.
Li M.; Liu T.; Li J.; He H.; Dai H.; Xie J. Visible-Light-Mediated Deoxyalkynylation of Activated Tertiary Alcohols. J. Org. Chem. 2021, 86, 12386–12393..
Not in our library10.1021/acs.joc.1c01356
1223.
Amos S. G. E.; Cavalli D.; Le Vaillant F.; Waser J. Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions. Angew. Chem., Int. Ed. 2021, 60, 23827–23834..
Not in our library10.1002/anie.202110257
1224.
Guo J.; Wang Y.; Li Y.; Lu K.; Liu S.; Wang W.; Zhang Y. Graphitic Carbon Nitride Polymer as a Recyclable Photoredox Catalyst for Decarboxylative Alkynylation of Carboxylic Acids. Adv. Synth. Catal. 2020, 362, 3898–3904..
Not in our library10.1002/adsc.202000777
1225.
Garreau M.; Le Vaillant F.; Waser J. C-Terminal Bioconjugation oif Peptides through Photoredox Catalyzed Decarboxylative Alkynylation. Angew. Chem., Int. Ed. 2019, 58, 8182–8186..
Not in our library10.1002/anie.201901922
1226.
Kawakami R.; Usui S.; Tada N.; Itoh A. Late-Stage Diversification Strategy for Synthesizing Ynamides through Copper-Catalyzed Diynylation and Azide-Alkyne Cycloaddition. Chem. Commun. 2023, 59, 450–453..
Not in our library10.1039/d2cc05575a
1227.
Declas N.; Maynard J. R. J.; Menin L.; Gasilova N.; Gotze S.; Sprague J. L.; Stallforth P.; Matile S.; Waser J. Tyrosine Bioconjugation with Hypervalent Iodine. Chem. Sci. 2022, 13, 12808–12817..
Not in our library10.1039/d2sc04558c
1228.
Sun X.; Guo X.-Q.; Chen L.-M.; Kang T.-R. Synthesis, Characterization of Spirocyclic λ3-Iodanes and Their Application to Prepare 4,1-Benzoxazepine-2,5-diones and 1,3-Diynes. Chem. - Eur. J. 2021, 27, 4312–4316..
Not in our library10.1002/chem.202005124
1229.
Ura T.; Shimbo D.; Yudasaka M.; Tada N.; Itoh A. Synthesis of Phenol-Derived cis-Vinyl Ethers Using Ethynyl Benziodoxolone. Chem. - Asian J. 2020, 15, 4000–4004..
Not in our library10.1002/asia.202001102
1230.
Wu J.; Deng X.; Yoshikai N. Stereocontrolled Synthesis of Halovinylbenziodoxoles by Hydro- and Iodochlorination of Ethynylbenziodoxoles. Chem. - Eur. J. 2019, 25, 7839–7842..
Not in our library10.1002/chem.201901543
1231.
Tessier R.; Ceballos J.; Guidotti N.; Simonet-Davin R.; Fierz B.; Waser J. ″Doubly Orthogonal″ Labeling of Peptides and Proteins. Chem. 2019, 5, 2243–2263..
Not in our library10.1016/j.chempr.2019.06.022
1232.
Shimbo D.; Shibata A.; Yudasaka M.; Maruyama T.; Tada N.; Uno B.; Itoh A. Synthesis of cis-β-Amidevinyl Benziodoxolones from the Ethynyl Benziodoxolone-Chloroform Complex and Sulfonamides. Org. Lett. 2019, 21, 9769–9773..
Not in our library10.1021/acs.orglett.9b03990
1233.
Caramenti P.; Declas N.; Tessier R.; Wodrich M. D.; Waser J. Stereoselective Synthesis of Alkyl-, Aryl-, Vinyl- and Alkynyl-Substituted Z-Enamides and Enol Ethers. Chem. Sci. 2019, 10, 3223–3230..
Not in our library10.1039/c8sc05573d
1234.
Wu J.; Xu K.; Hirao H.; Yoshikai N. Pd-Catalyzed, Ligand-Enabled Stereoselective 1,2-Iodine(III) Shift/1,1-Carboxyalkynylation of Alkynylbenziodoxoles. Chem. - Eur. J. 2017, 23, 1521–1525..
Not in our library10.1002/chem.201605772
1235.
Wu J.; Deng X.; Hirao H.; Yoshikai N. Pd-Catalyzed Conversion of Alkynyl-λ3-iodanes to Alkenyl-λ3-iodanes via Stereoselective 1,2-Iodine(III) Shift/1,1-Hydrocarboxylation. J. Am. Chem. Soc. 2016, 138, 9105–9108..
Not in our library10.1021/jacs.6b06247
1236.
Kitamura T.; Sato R.; Morita H.; Kitamura D.; Oyamada J.; Higashi M.; Kishikawa Y. Convenient Access to Stable Β-Fluorovinyl-Substituted 1,2-Benziodoxolones. ARKIVOC 2021, 2020 (iv), 25–34..
Not in our library10.24820/ark.5550190.p011.291
1237.
Stridfeldt E.; Seemann A.; Bouma M. J.; Dey C.; Ertan A.; Olofsson B. Synthesis, Characterization and Unusual Reactivity of Vinylbenziodoxolones-Novel Hypervalent Iodine Reagents. Chem. - Eur. J. 2016, 22, 16066–16070..
Not in our library10.1002/chem.201603955
1238.
Wang C.-S.; Tan P. S. L.; Ding W.; Ito S.; Yoshikai N. Regio- and Stereoselective Synthesis of Enol Carboxylate, Phosphate, and Sulfonate Esters via Iodo(III)functionalization of Alkynes. Org. Lett. 2022, 24, 430–434..
Not in our library10.1021/acs.orglett.1c04123
1239.
Laskar R. A.; Ding W.; Yoshikai N. Iodo(III)-Meyer-Schuster Rearrangement of Propargylic Alcohols Promoted by Benziodoxole Triflate. Org. Lett. 2021, 23, 1113–1117..
Not in our library10.1021/acs.orglett.1c00039
1240.
Ding W.; Chai J.; Wang C.; Wu J.; Yoshikai N. Stereoselective Access to Highly Substituted Vinyl Ethers via trans-Difunctionalization of Alkynes with Alcohols and Iodine(III) Electrophile. J. Am. Chem. Soc. 2020, 142, 8619–8624..
Not in our library10.1021/jacs.0c04140
1241.
Chai J.; Ding W.; Wu J.; Yoshikai N. Fluorobenziodoxole-BF3 Reagent for Iodo(III)etherification of Alkynes in Ethereal Solvent. Chem. - Asian J. 2020, 15, 2166–2169..
Not in our library10.1002/asia.202000653
1242.
Milzarek T. M.; Waser J. Synthesis of Trifluoromethylated Alkenes: Hypervalent Iodine Meets High-Valent Copper. Angew. Chem., Int. Ed. 2023, 62, e202306128.
Not in our library10.1002/anie.202306128
1243.
Bhaskar Pal K.; Di Tommaso E. M.; Inge A. K.; Olofsson B. Stereospecific Photoredox-Catalyzed Vinylation to Functionalized Alkenes and C-Glycosides. Angew. Chem., Int. Ed. 2023, 62, e202301368.
Not in our library10.1002/anie.202301368
1244.
Pisella G.; Gagnebin A.; Waser J. Copper-Catalyzed Oxyvinylation of Diazo Compounds. Org. Lett. 2020, 22, 3884–3889..
Not in our library10.1021/acs.orglett.0c01150
1245.
Declas N.; Waser J. Access to Vinyl Ethers and Ketones with Hypervalent Iodine Reagents as Oxy-Allyl Cation Synthetic Equivalents. Angew. Chem., Int. Ed. 2020, 59, 18256–18260..
Not in our library10.1002/anie.202006707
1246.
Castoldi L.; Di Tommaso E. M.; Reitti M.; Graefen B.; Olofsson B. Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions. Angew. Chem., Int. Ed. 2020, 59, 15512–15516..
Not in our library10.1002/anie.202002936
1247.
Boelke A.; Caspers L. D.; Nachtsheim B. J. NH2-Directed C-H Alkenylation of 2-Vinylanilines with Vinylbenziodoxolones. Org. Lett. 2017, 19, 5344–5347..
Not in our library10.1021/acs.orglett.7b02630
1248.
Castoldi L.; Rajkiewicz A. A.; Olofsson B. Transition Metal-Free and Regioselective Vinylation of Phosphine Oxides and H-Phosphinates with VBX Reagents. Chem. Commun. 2020, 56, 14389–14392..
Not in our library10.1039/d0cc05992g
1249.
Zhdankin V. V.; Protasiewicz J. D. Development of New Hypervalent Iodine Reagents with Improved Properties and Reactivity by Redirecting Secondary Bonds at Iodine Center. Coord. Chem. Rev. 2014, 275, 54–62..
Not in our library10.1016/j.ccr.2014.04.007
1250.
Yoshimura A.; Huss C. D.; Liebl M.; Rohde G. T.; Larson S. M.; Frahm G. B.; Luedtke M. W.; Schumacher T. J.; Gardner Z. S.; Zhdankin V. V.; Postnikov P. S.; Yusubov M. S.; Kitamura T.; Saito A. Preparation, Structure, and Reactivity of Pseudocyclic β-Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives. Adv. Synth. Catal. 2021, 363, 3365–3371..
Not in our library10.1002/adsc.202100341
1251.
Watanabe K.; Moriyama K. Copper-Catalyzed Indole-Selective C-N Coupling Reaction of Indolyl(2-alkoxy-phenyl)iodonium Imides: Effect of Substituent on Iodoarene as Dummy Ligand. J. Org. Chem. 2018, 83, 14827–14833..
Not in our library10.1021/acs.joc.8b02676
1252.
Wang Z.; Herraiz A. G.; del Hoyo A. M.; Suero M. G. Generating Carbyne Equivalents with Photoredox Catalysis. Nature 2018, 554, 86–91..
Not in our library10.1038/nature25185
1253.
Yoshimura A.; Klasen S. C.; Shea M. T.; Nguyen K. C.; Rohde G. T.; Saito A.; Postnikov P. S.; Yusubov M. S.; Nemykin V. N.; Zhdankin V. V. Preparation, Structure, and Reactivity of Pseudocyclic Benziodoxole Tosylates: New Hypervalent Iodine Oxidants and Electrophiles. Chem. - Eur. J. 2017, 23, 691–695..
Not in our library10.1002/chem.201604475
1254.
Yoshimura A.; Larson S. M.; Frahm G. B.; Huss C. D.; Rohde G. T.; Nemykin V. N.; Yusubov M. S.; Saito A.; Zhdankin V. V. Synthesis of Arylbenziodoxoles Using Pseudocyclic Benziodoxole Triflate and Arenes. ARKIVOC 2021, 2020 (iv), 35–49..
Not in our library10.24820/ark.5550190.p011.324
1255.
Qurban J.; Elsherbini M.; Alharbi H.; Wirth T. Synthesis, Characterization and Reactivity of Novel Pseudocyclic Hypervalent Iodine Reagents with Heteroaryl Carbonyl Substituents. Chem. Commun. 2019, 55, 7998–8000..
Not in our library10.1039/c9cc03905h
1256.
Vlasenko Y. A.; Postnikov P. S.; Trusova M. E.; Shafir A.; Zhdankin V. V.; Yoshimura A.; Yusubov M. S. Synthesis of Five-Membered Iodine-Nitrogen Heterocycles from Benzimidazole-Based Iodonium Salts. J. Org. Chem. 2018, 83, 12056–12070..
Not in our library10.1021/acs.joc.8b01995
1257.
Boelke A.; Lork E.; Nachtsheim B. J. N-Heterocycle-Stabilized Iodanes: From Structure to Reactivity. Chem. - Eur. J. 2018, 24, 18653–18657..
Not in our library10.1002/chem.201804957
1258.
Boelke A.; Sadat S.; Lork E.; Nachtsheim B. J. Pseudocyclic bis-N-Heterocycle-Stabilized Iodanes - Synthesis, Characterization and Applications. Chem. Commun. 2021, 57, 7434–7437..
Not in our library10.1039/d1cc03097c
1259.
Yoshimura A.; Huss C. D.; Saito A.; Kitamura T.; Zhdankin V. V. 2-Iodosylbenzoic Acid Activated by Trifluoromethanesulfonic Anhydride: Efficient Oxidant and Electrophilic Reagent for Preparation of Iodonium Salts. New J. Chem. 2021, 45, 16434–16437..
Not in our library10.1039/d1nj03787k
1260.
Tu H.-F.; Jeandin A.; Suero M. G. Catalytic Synthesis of Cyclopropenium Cations with Rh-Carbynoids. J. Am. Chem. Soc. 2022, 144, 16737–16743..
Not in our library10.1021/jacs.2c07769
1261.
Yoshimura A.; Ngo K.; Mironova I. A.; Gardner Z. S.; Rohde G. T.; Ogura N.; Ueki A.; Yusubov M. S.; Saito A.; Zhdankin V. V. Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides. Org. Lett. 2024, 26, 1891–1895..
Not in our library10.1021/acs.orglett.4c00197
1262.
Parra A. Chiral Hypervalent Iodines: Active Players in Asymmetric Synthesis. Chem. Rev. 2019, 119, 12033–12088..
Not in our library10.1021/acs.chemrev.9b00338
1263.
Yusubov M. S.; Zhdankin V. V. Iodine Catalysis: a Green Alternative to Transition Metals in Organic Chemistry and Technology. Resource-Efficient Technologies 2015, 1, 49–67..
Not in our library10.1016/j.reffit.2015.06.001
1264.
Ochiai M.; Takeuchi Y.; Katayama T.; Sueda T.; Miyamoto K. Iodobenzene-Catalyzed alpha -Acetoxylation of Ketones. In Situ Generation of Hypervalent (Diacyloxyiodo)benzenes Using m-Chloroperbenzoic Acid. J. Am. Chem. Soc. 2005, 127, 12244–12245..
Not in our library10.1021/ja0542800
1265.
Dohi T.; Maruyama A.; Yoshimura M.; Morimoto K.; Tohma H.; Kita Y. Versatile Hypervalent-Iodine(III)-Catalyzed Oxidations with m-Chloroperbenzoic acid as a Cooxidant. Angew. Chem., Int. Ed. 2005, 44, 6193–6196..
Not in our library10.1002/anie.200501688
1266.
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