Shining light on photoredox catalysis: Theory and synthetic applications

Journal of Organic Chemistry

Volumn 77, Issue 4, 2012, Pages 1617-1622

  Tucker, Joseph W ^a   Stephenson, Corey R J ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC TRANSFORMATIONS; PHOTOELECTRONIC PROPERTIES; PHOTOREDOX CATALYSIS; SYNTHETIC APPLICATION; SYNTHETIC ORGANIC CHEMISTRY;

CHEMISTRY; ORGANIC COMPOUNDS;

CATALYSIS;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; ELECTRON TRANSPORT; ORGANIC CHEMISTRY; OXIDATION REDUCTION REACTION; PHOTOCATALYSIS; PHOTOREDOX CATALYSIS; SYNTHESIS; THERMODYNAMICS;

EID: 84857230386     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202538x     Document Type: Article

References (76)

1. Banerjee, R.; Becker, D.; Dickman, M.; Gladyshev, V.; Ragsdale, S. Redox Biochemistry; Wiley-VCH Verlag GmbH: Weinheim, 2007.
2. Hudlicky, M. Oxidations in Organic Chemistry; Monograph 186; American Chemical Society: Washington DC, 1990.
3. Hudlicky, M. Reductions in Organic Chemistry, 2 nd ed.; Monograph 188; American Chemical Society: Washington DC, 1996.
4. Burstall, F. H. J. Chem. Soc. 1936, 173
5. Flamigni, L.; Barieri, A.; Sabatini, C.; Ventura, B.; Barigelletti, F. Top. Curr. Chem. 2007, 281, 143
6. Campagna, S.; Puntoriero, F.; Nastasi, F.; Bergamini, G.; Balzani, V. Top. Curr. Chem. 2007, 280, 117
7. Meyer, T. J. Acc. Chem. Res. 1989, 22, 163
8. Bard, A. J.; Fox, M. A. Acc. Chem. Res. 1995, 28, 141
9. O'Regan, B.; Grätzel, M. Nature 1991, 353, 737
10. Gray, H. B.; Maverick, A. W. Science 1981, 214, 1201
11. Hedstrand, D. M.; Kruizinga, W. H.; Kellogg, R. M. Tetrahedron Lett. 1978, 19, 1255
12. Ciamician, G. Science 1912, 36, 385
13. Albini, A.; Fagnoni, M. Green Chem. 2004, 6, 1
14. Mchedolv-Petrosyan, N. O.; Kukhtik, V. I.; Egorova, S. I. Russ. J. Gen. Chem. 2006, 76, 1607
15. o ranges between 575-1000 ns in various organic and aqueous solvents, see: Ding, Z.; Wellington, R. G.; Brevet, P. F.; Girault, H. H. J. Phys. Chem. 1996, 100, 10658
16. Wrighton, M.; Markham, J. J. Phys. Chem. 1973, 77, 3042
17. Demas, J. N.; Harris, E. W.; McBride, R. P. J. Am. Chem. Soc. 1977, 99, 3547
18. All potentials presented in this text are presented with respect to the saturated calomel electrode (SCE), unless otherwise noted. For conversion between various reference electrodes, see: Pavlishchuk, V. V.; Addison, A. W. Inorg. Chim. Acta 2000, 298, 97
19. Sullivan, B. P.; Salmon, D. J.; Meyer, T. J.; Peedin, J. Inorg. Chem. 1979, 18, 3369
20. Haga, M.-A.; Dodsworth, E. S.; Eryavec, G.; Seymour, P.; Lever, A. B. P. Inorg. Chem. 1985, 24, 1901
21. Wacholtz, W. F.; Auerbach, R. A.; Schmehl, R. H. Inorg. Chem. 1986, 25, 227
22. Weiner, M. A.; Basu, A. Inorg. Chem. 1980, 19, 2797
23. Balzani, V.; Bolletta, F.; Gandolfi, M. T.; Maestri, M. Top. Curr. Chem. 1978, 75, 1
24. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259
25. Juris, A.; Balzani, v.; Belser, P.; von Zelewsky, A. Helv. Chim. Acta 1981, 64, 2175
26. Scandola, F.; Indelli, M. T. Pure Appl. Chem. 1988, 60, 973
27. Bignozzi, C. A.; Scandola, F. Inorg. Chem. 1984, 23, 1540
28. Arbogast, J. W.; Foote, C. S.; Kao, M. J. Am. Chem. Soc. 1992, 114, 2277
29. Vanýsek, P. Electrochemical Series. In CRC Handbook of Chemistry and Physics, 83 rd ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, 2002; pp 8-21-8-31.
30. Slinker, J. D.; Gorodetsky, A. A.; Lowry, M. S.; Wang, J.; Parker, S.; Rohl, R.; Bernhard, S.; Malliaras, G. G. J. Am. Chem. Soc. 2004, 126, 2763
31. Hoffman, M. Z. J. Phys. Chem. 1988, 92, 3458
32. Marcus, R. A. J. Chem. Phys. 1956, 24, 966
33. The electronic coupling is a parameter describing the overlap of the reaction partner's electronic wave functions and gives an indication of the probability of the electron transfer occurring; see: Newton, M. D.; Sutin, N. Annu. Rev. Phys. Chem. 1984, 35, 437
34. Closs, G. L.; Miller, J. R. Science 1988, 240, 440
35. Quiclet-Sire, B.; Zard, S. Z. Pure. Appl. Chem. 2011, 83, 519
36. Beemelmanns, C.; Reissig, H.-U. Chem. Soc. Rev. 2011, 40, 2199
37. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102
38. Teplý, F. Collect. Czech. Chem. Commun. 2011, 76, 859
39. Narayanam, J. M. R.; Tucker, J. W; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756
40. Condie, A. G.; González-Gómez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2010, 132, 1464
41. Rueping, M.; Vial, C.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C. Chem. Commun. 2011, 47, 2360
42. Xuan, J.; Cheng, Y.; An, J.; Lu, L.-Q.; Zhang, X.-X.; Xiao, W.-J. Chem. Commun. 2011, 47, 8337
43. Rueping, M.; Zhu, S.; Koenigs, R. M. Chem. Commun. 2011, 47, 8679
44. Zou, Y.-Q.; Lu, L.-Q.; Fu, L.; Chang, N.-J.; Rong, J.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2011, 50, 7171
45. Rueping, M.; Leonori, D.; Poisson, T. Chem. Commun. 2011, 47, 9615
46. Freeman, D. B.; Furst, L.; Condie, A. G.; Stephenson, C. R. J. Org. Lett. 2012, 14, 94
47. For a similar oxidative generation of oxocarbenium intermediates, see: Tucker, J. W.; Narayanam, J. M. R.; Shah, P. S.; Stephenson, C. R. J. Chem. Commun. 2011, 47, 5040
48. McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114
49. For the fragmentation and annulation reactions of cyclopropyl ammoniumyl radical cations, see: Maity, S.; Zhu, M.; Shinabery, R. S.; Zheng, N. Angew. Chem., Int. Ed. 2012, 51, 222
50. Ischay, M. A.; Lu, Z.; Yoon, T. P. J. Am. Chem. Soc. 2010, 132, 8572
51. Lin, S.; Ischay, M. A.; Fry, C. G.; Yoon, T. P. J. Am. Chem. Soc. 2011, 133, 19350
52. Cano-Yelo, H.; Deronzier, A. J. Chem. Soc., Perkin Trans. 2 1984, 1093
53. Calculated from values in: DeLaive, P. J.; Lee, J. T.; Sprintschnik, H. W.; Abruña, H.; Meyer, T. J.; Whitten, D. G. J. Am. Chem. Soc. 1977, 99, 7094
54. Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18566
55. Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77
56. Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875
57. For the perfluoroalkylation of silyl enol ethers mediated by photoredox catalysis, see: Pham, P. V.; Nagib, D. A.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2011, 50, 6119
58. 2Cl, see: Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224
59. Shih, H.-W.; Vander Wal, M. N.; Grange, R. L.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 13600
60. For the reduction of halomethanes and the subsequent reaction with DMF to form Vilsmeier-Haack reagents, see: Dai, C.; Narayanam, J. M. R.; Stephenson, C. R. J. Nature Chem. 2011, 3, 140
61. Tucker, J. W.; Narayanam, J. M. R.; Krabbe, S. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 368
62. Furst, L.; Matsuura, B. S.; Narayanm, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 3104
63. Tucker, J. W.; Nguyen, J. D.; Narayanam, J. M. R.; Krabbe, S. W.; Stephenson, C. R. J. Chem. Commun. 2010, 46, 4985
64. Tucker, J. W.; Stephenson, C. R. J. Org. Lett. 2011, 13, 5468
65. Furst, L.; Narayanam, J. M. R.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2011, 50, 9655
66. Andrews, R. S.; Becker, J. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2010, 49, 7274
67. Andrews, R. S.; Becker, J. J.; Gagné, M. R. Org. Lett. 2011, 13, 2406
68. Sun, H.; Yoshimura, A.; Hoffman, M. Z. J. Phys. Chem. 1994, 98, 5058
69. Barton, D. H. R.; Csiba, M. A.; Jaszberenyi, J. C. Tetrahedron Lett. 1994, 35, 2869
70. Nguyen, J. D.; Tucker, J. W.; Konieczynska, M. D.; Stephenson, C. R. J. J. Am. Chem. Soc. 2011, 133, 4160
71. Okada, K.; Okubo, K.; Morita, N.; Oda, M. Chem. Lett. 1993, 2021 and references therein
72. Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886
73. Hurtley, A. E.; Cismesia, M. A.; Ischay, M. A.; Yoon, T. P. Tetrahedron 2011, 67, 4442
74. Lu, Z.; Shen, M.; Yoon, T. P. J. Am. Chem. Soc. 2011, 133, 1162
75. Du, J.; Espelt, L. R.; Guzei, I. A.; Yoon, T. P. Chem. Sci. 2011, 2, 2115
76. Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2009, 131, 14604