Skip to content
naulon

No retraction, correction or concern found when last checked on Nov 2, 2026.

Visible‐Light‐Mediated Generation of Nitrogen‐Centered Radicals: Metal‐Free Hydroimination and Iminohydroxylation Cyclization Reactions

Jacob Davies, Samuel G. Booth, Stephanie Essafi and 2 more

Angewandte Chemie International Edition · 2015

doi:10.1002/anie.201507641

Abstract

The formation and use of iminyl radicals in novel and divergent hydroimination and iminohydroxylation cyclization reactions has been accomplished through the design of a new class of reactive O ‐aryl oximes. Owing to their low reduction potentials, the inexpensive organic dye eosin Y could be used as the photocatalyst of the organocatalytic hydroimination reaction. Furthermore, reaction conditions for a unique iminohydroxylation were identified; visible‐light‐mediated electron transfer from novel electron donor–acceptor complexes of the oximes and Et 3 N was proposed as a key step of this process.

Shown for reading. Its publisher allows quoting it, not republishing it.

References 74

  1. 1.

    Zard SZ. Chem. Soc. Rev. 2008;37:1603.

    Not in our library10.1039/b613443m

  2. 2.

    Cassayre J, Gagosz F, Zard SS. Angew. Chem. Int. Ed. 2002;41:1783.

    Not in our library10.1002/1521-3773(20020517)41:10<1783::aid-anie1783>3.0.co;2-i

  3. 3.

    Angew. Chem. 2002;114.

    Not in our library

  4. 4.

    Sharp L, Zard SZ. Org. Lett. 2006;8:831.

    Not in our library10.1021/ol052749q

  5. 5.

    Faulkner A, Race NJ, Scott JS, Bower JF. Chem. Sci. 2014;5:2416.

    Not in our library

  6. 6.

    Bingham M, Moutrille C, Zard SS. Heterocycles. 2014;88:953.

    Not in our library

  7. 7.

    Kitamura M, Shintaku Y, Kudo D, Okauchi T. Tetrahedron Lett. 2010;51:4890.

    Not in our library

  8. 8.

    Minozzi M, Nanni D, Spagnolo P. Chem. Eur. J. 2009;15:7830.

    Not in our library10.1002/chem.200802710

  9. 9.

    Beaume A, Courillon C, Derat E, Malacria M. Chem. Eur. J. 2008;14:1238.

    Not in our library10.1002/chem.200700884

  10. 10.

    Noack M, Göttlich R. Chem. Commun. 2002;536.

    Not in our library10.1039/b111656h

  11. 11.

    Guindon Y, Guerin B, Landry SR. Org. Lett. 2001;3:2293.

    Not in our library10.1021/ol0160809

  12. 12.

    Lin X, Artman GD, Stien D, Weinreb SM. Tetrahedron. 2001;57:8779.

    Not in our library

  13. 13.

    Welsch ME, Snyder SA, Stockwell BR. Curr. Opin. Chem. Biol. 2010;14:347.

    Not in our library10.1016/j.cbpa.2010.02.018

  14. 14.

    Prier CK, Rankic DA, MacMillan DWC. Chem. Rev. 2013;113:5322.

    Not in our library10.1021/cr300503r

  15. 15.

    Xi Y, Yi H, Lei A. Org. Biomol. Chem. 2013;11:2387.

    Not in our library10.1039/c3ob40137e

  16. 16.

    Hopkinson MN, Sahoo B, Li J-L, Glorius F. Chem. Eur. J. 2014;20:3874.

    Not in our library10.1002/chem.201304823

  17. 17.

    Narayanam JMR, Stephenson C. Chem. Soc. Rev. 2011;40:102.

    Not in our library10.1039/b913880n

  18. 18.

    Cecere G, König CM, Alleva JL, MacMillan DWC. J. Am. Chem. Soc. 2013;135:11521.

    Not in our library10.1021/ja406181e

  19. 19.

    Allen LJ, Cabrera PJ, Lee M, Sanford MS. J. Am. Chem. Soc. 2014;136:5607.

    Not in our library10.1021/ja501906x

  20. 20.

    Kim H, Kim T, Lee DG, Roh SW, Lee C. Chem. Commun. 2014;50:9273.

    Not in our library10.1039/c4cc03905j

  21. 21.

    Qin Q, Yu S. Org. Lett. 2014;16:3504.

    Not in our library10.1021/ol501457s

  22. 22.

    Song L, Zhang L, Luo S, Cheng J-P. Chem. Eur. J. 2014;20:14231.

    Not in our library10.1002/chem.201404479

  23. 23.

    Maity S, Zheng N. Angew. Chem. Int. Ed. 2012;51:9562.

    Not in our library10.1002/anie.201205137

  24. 24.

    Angew. Chem. 2012;124.

    Not in our library

  25. 25.

    This reference’s wording can’t be shown under the paper’s licence.

    Not in our library

  26. 26.

    Musacchio AJ, Nguyen LQ, Beard H, Knowles RR. J. Am. Chem. Soc. 2014;136:12217.

    Not in our library10.1021/ja5056774

  27. 27.

    Atmaram S, Forrester AR, Gill M, Thomson RH. J. Chem. Soc. Perkin Trans. 1. 1981;1721.

    Not in our library

  28. 28.

    Forrester AR, Gill M, Sadd JS, Thomson RH. J. Chem. Soc. Perkin Trans. 1. 1979;612.

    Not in our library

  29. 29.

    Mikami KNT. Chem. Lett. 2000;338.

    Not in our library

  30. 30.

    Kitamura M, Narasaka K. Bull. Chem. Soc. Jpn. 2008;81:539.

    Not in our library

  31. 31.

    McBurney RT, Walton JC. J. Am. Chem. Soc. 2013;135:7349.

    Not in our library10.1021/ja402833w

  32. 32.

    Walton JC. Acc. Chem. Res. 2014;47:1406.

    Not in our library10.1021/ar500017f

  33. 33.

    Jiang H, An X, Tong K, Zheng T, Zhang Y, Yu S. Angew. Chem. Int. Ed. 2015;54:4055.

    Not in our library10.1002/anie.201411342

  34. 34.

    Angew. Chem. 2015;127.

    Not in our library

  35. 35.

    Ravelli D, Fagnoni M, Albini A. Chem. Soc. Rev. 2013;42:97.

    Not in our library10.1039/c2cs35250h

  36. 36.

    Brimioulle R, Lenhart D, Maturi MM, Bach T. Angew. Chem. Int. Ed. 2015;54:3872.

    Not in our library10.1002/anie.201411409

  37. 37.

    Angew. Chem. 2015;127.

    Not in our library

  38. 38.

    Wilger DJ, Grandjean J-MM, Lammert TR, Nicewicz DA. Nat. Chem. 2014;6:720.

    Not in our library10.1038/nchem.2000

  39. 39.

    Hari DP, Schroll P, König B. J. Am. Chem. Soc. 2012;134:2958.

    Not in our library10.1021/ja212099r

  40. 40.

    Neumann M, Fuldner S, König B, Zeitler K. Angew. Chem. Int. Ed. 2011;50:951.

    Not in our library10.1002/anie.201002992

All 74 references

Cited by papers we hold 4

Reads

Read by people on this page

None yet.

Checked or read by AI through naulon

None yet.

A person counts once a day per paper. We keep no cookie and no address: a reader is a hash that changes every day. Any month under five reads shows no number.

Are you an author?

Is this your paper?

Claim it to add your note and be paid when agents cite it. Free.