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

Angewandte Chemie - International Edition

Volumn 54, Issue 47, 2015, Pages 14017-14021

  Davies, Jacob ^a   Booth, Samuel G ^a   Essafi, Stephanie ^b   Dryfe, Robert A W ^a   Leonori, Daniele ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

electron transfer; hydroimination; iminohydroxylation; photoredox catalysis; visible light

Indexed keywords

CHARGE TRANSFER; ELECTRON TRANSITIONS; FREE RADICAL REACTIONS; LIGHT; NITROGEN;

ELECTRON TRANSFER; HYDROIMINATION; IMINOHYDROXYLATION; PHOTOREDOX CATALYSIS; VISIBLE LIGHT;

CYCLIZATION;

EID: 84954431494     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201507641     Document Type: Article

References (73)

1. S. Z. Zard, Chem. Soc. Rev. 2008, 37, 1603; for selected examples of NCRs in synthesis, see:
2. J. Cassayre, F. Gagosz, S. S. Zard, Angew. Chem. Int. Ed. 2002, 41, 1783;
3. Angew. Chem. 2002, 114, 1861;
4. L. Sharp, S. Z. Zard, Org. Lett. 2006, 8, 831.
5. A. Faulkner, N. J. Race, J. S. Scott, J. F. Bower, Chem. Sci. 2014, 5, 2416;
6. M. Bingham, C. Moutrille, S. S. Zard, Heterocycles 2014, 88, 953;
7. M. Kitamura, Y. Shintaku, D. Kudo, T. Okauchi, Tetrahedron Lett. 2010, 51, 4890;
8. M. Minozzi, D. Nanni, P. Spagnolo, Chem. Eur. J. 2009, 15, 7830;
9. A. Beaume, C. Courillon, E. Derat, M. Malacria, Chem. Eur. J. 2008, 14, 1238;
10. M. Noack, R. Göttlich, Chem. Commun. 2002, 536;
11. Y. Guindon, B. Guerin, S. R. Landry, Org. Lett. 2001, 3, 2293;
12. X. Lin, G. D. Artman III, D. Stien, S. M. Weinreb, Tetrahedron 2001, 57, 8779.
13. M. E. Welsch, S. A. Snyder, B. R. Stockwell, Curr. Opin. Chem. Biol. 2010, 14, 347.
14. C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113, 5322;
15. Y. Xi, H. Yi, A. Lei, Org. Biomol. Chem. 2013, 11, 2387;
16. M. N. Hopkinson, B. Sahoo, J.-L. Li, F. Glorius, Chem. Eur. J. 2014, 20, 3874;
17. J. M. R. Narayanam, C. Stephenson, Chem. Soc. Rev. 2011, 40, 102.
18. G. Cecere, C. M. König, J. L. Alleva, D. W. C. MacMillan, J. Am. Chem. Soc. 2013, 135, 11521.
19. L. J. Allen, P. J. Cabrera, M. Lee, M. S. Sanford, J. Am. Chem. Soc. 2014, 136, 5607.
20. H. Kim, T. Kim, D. G. Lee, S. W. Roh, C. Lee, Chem. Commun. 2014, 50, 9273.
21. Q. Qin, S. Yu, Org. Lett. 2014, 16, 3504.
22. L. Song, L. Zhang, S. Luo, J.-P. Cheng, Chem. Eur. J. 2014, 20, 14231.
23. S. Maity, N. Zheng, Angew. Chem. Int. Ed. 2012, 51, 9562;
24. Angew. Chem. 2012, 124, 9700;
25. J. Wang, N. Zheng, Angew. Chem. Int. Ed. 2015, DOI: 10.1002/anie.201504076; Angew. Chem. 2015, DOI: 10.1002/ange.201504076.
26. A. J. Musacchio, L. Q. Nguyen, H. Beard, R. R. Knowles, J. Am. Chem. Soc. 2014, 136, 12217.
27. S. Atmaram, A. R. Forrester, M. Gill, R. H. Thomson, J. Chem. Soc. Perkin Trans. 1 1981, 1721;
28. A. R. Forrester, M. Gill, J. S. Sadd, R. H. Thomson, J. Chem. Soc. Perkin Trans. 1 1979, 612.
29. K. N. T. Mikami, Chem. Lett. 2000, 338;
30. M. Kitamura, K. Narasaka, Bull. Chem. Soc. Jpn. 2008, 81, 539.
31. R. T. McBurney, J. C. Walton, J. Am. Chem. Soc. 2013, 135, 7349;
32. J. C. Walton, Acc. Chem. Res. 2014, 47, 1406.
33. 3] and para-trifluoromethylbenzoyl acyl oximes and their addition to aromatic compounds; see:, H. Jiang, X. An, K. Tong, T. Zheng, Y. Zhang, S. Yu, Angew. Chem. Int. Ed. 2015, 54, 4055;
34. Angew. Chem. 2015, 127, 4127.
35. D. Ravelli, M. Fagnoni, A. Albini, Chem. Soc. Rev. 2013, 42, 97;
36. R. Brimioulle, D. Lenhart, M. M. Maturi, T. Bach, Angew. Chem. Int. Ed. 2015, 54, 3872;
37. Angew. Chem. 2015, 127, 3944; for selected examples, see:
38. D. J. Wilger, J.-M. M. Grandjean, T. R. Lammert, D. A. Nicewicz, Nat. Chem. 2014, 6, 720;
39. D. P. Hari, P. Schroll, B. König, J. Am. Chem. Soc. 2012, 134, 2958;
40. M. Neumann, S. Fuldner, B. König, K. Zeitler, Angew. Chem. Int. Ed. 2011, 50, 951;
41. Angew. Chem. 2011, 123, 981;
42. A. Bauer, F. Westkmäper, S. Grimme, T. Bach, Nature 2005, 436, 1139;
43. R. Brimioulle, T. Bach, Science 2013, 342, 6160.
44. M. Wakasa, Y. Sakaguchi, J. Nakamura, H. Hayashi, J. Phys. Chem. 1992, 96, 9651.
45. J. A. Terrett, M. D. Clift, D. W. C. MacMillan, J. Am. Chem. Soc. 2014, 136, 6858;
46. Z. Zuo, D. W. C. MacMillan, J. Am. Chem. Soc. 2014, 136, 5257;
47. A. McNally, C. K. Prier, D. W. C. MacMillan, Science 2011, 334, 1114;
48. M. T. Pirnot, D. A. Rankic, D. B. C. Martin, D. W. C. MacMillan, Science 2013, 339, 1593.
49. A. Vogler, H. Kunkely, Coord. Chem. Rev. 2000, 208, 321.
50. E. D. Lorance, W. H. Kramer, I. R. Gould, J. Am. Chem. Soc. 2002, 124, 15225;
51. Y.-R. Luo, Handbook of Bond Dissociation Energies in Organic Compounds, CRC Press, Boca Raton, 2003.
52. J. B. Boivin, E. Fouquet, S. Z. Zard, Tetrahedron 1994, 50, 1745.
53. F. Agabito, P. M. Nunes, B. J. Costa Cabral, R. M. Borges dos Santos, J. A. Martinho Simões, J. Org. Chem. 2007, 72, 8770.
54. D. P. Hari, B. König, Chem. Commun. 2014, 50, 6688.
55. S. V. Rosokha, J. K. Kochi, Acc. Chem. Res. 2008, 41, 641;
56. R. Rathore, S. V. Lindeman, J. K. Kochi, J. Am. Chem. Soc. 1997, 119, 9393.
57. J. Cossy, D. Belotti, Tetrahedron 2006, 62, 6459.
58. S. R. Kandukuri, A. Bahamonde, I. Chatterjee, I. D. Jurberg, E. C. Escudero-Adan, P. Melchiorre, Angew. Chem. Int. Ed. 2015, 54, 1485;
59. Angew. Chem. 2015, 127, 1505;
60. E. Arceo, I. D. Jurberg, A. Alvarez-Fernadez, P. Melchiorre, Nat. Chem. 2013, 5, 750;
61. M. Nappi, G. Bergonzini, P. Melchiorre, Angew. Chem. Int. Ed. 2014, 53, 4921;
62. Angew. Chem. 2014, 126, 5021.
63. G. J. Kavarnos, N. J. Turro, Chem. Rev. 1986, 86, 401;
64. J. Mattay, Angew. Chem. Int. Ed. Engl. 1987, 26, 825;
65. Angew. Chem. 1987, 99, 849; for selected examples, see:
66. G. Berionni, P.-A. Bertelle, J. Marrot, R. Goumont, J. Am. Chem. Soc. 2009, 131, 18224;
67. S. Nad, H. Pal, J. Phys. Chem. A 2000, 104, 673.
68. C. Costentin, M. Robert, J.-M. Saveant, Chem. Phys. 2006, 324, 40.
69. S. Farid, J. P. Dinnocenzo, P. B. Merkel, R. H. Young, D. Shukla, G. Guirado, J. Am. Chem. Soc. 2011, 133, 11580.
70. N. J. Turro, R. Engel, J. Am. Chem. Soc. 1969, 91, 7113;
71. T. Abe, A. Kawai, Y. Kaji, K. Shibuya, K. Obi, J. Phys. Chem. A 1999, 103, 1457.
72. Y. Zhang, Y. Du, Z. Huang, J. Xu, X. Wu, Y. Wang, M. Wang, S. Yang, R. D. Webster, Y. R. Chi, J. Am. Chem. Soc. 2015, 137, 2416;
73. N. A. White, T. Rovis, J. Am. Chem. Soc. 2014, 136, 14674.