Visible light photoredox catalysis with transition metal complexes: Applications in organic synthesis

Chemical Reviews

Volumn 113, Issue 7, 2013, Pages 5322-5363

  Prier, Christopher K ^a   Rankic, Danica A ^a   MacMillan, David W C ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METAL TO LIGAND CHARGE TRANSFERS; ORGANIC SYNTHESIS; ORGANIC TRANSFORMATIONS; OXIDATION STATE; PHOTOREDOX CATALYSIS; SEMICONDUCTOR PHOTOCATALYSIS; SINGLE ELECTRON; VISIBLE-LIGHT PHOTOCATALYSTS;

CATALYSIS; LIGANDS; METAL COMPLEXES; PHOTOCATALYSTS; TRANSITION METAL COMPOUNDS;

RUTHENIUM;

ALKENE; COORDINATION COMPOUND; ORGANOMETALLIC COMPOUND; TRANSITION ELEMENT; TRIS(2,2' BIPYRIDYL)RUTHENIUM(II); TRIS(2,2'-BIPYRIDYL)RUTHENIUM(II);

CATALYSIS; CHEMISTRY; CYCLOADDITION; LIGHT; OXIDATION REDUCTION REACTION; REVIEW;

ALKENES; CATALYSIS; COORDINATION COMPLEXES; CYCLOADDITION REACTION; LIGHT; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; TRANSITION ELEMENTS;

EID: 84880124916     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr300503r     Document Type: Review

References (291)

1. Kalyanasundaram, K. Coord. Chem. Rev. 1982, 46, 159
2. Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P.; von Zelewsky, A. Coord. Chem. Rev. 1988, 84, 85
3. Juris, A.; Balzani, V.; Belser, P.; von Zelewsky, A. Helv. Chim. Acta 1981, 64, 2175
4. Grätzel, M. Acc. Chem. Res. 1981, 14, 376
5. Meyer, T. J. Acc. Chem. Res. 1989, 22, 163
6. Takeda, H.; Ishitani, O. Coord. Chem. Rev. 2010, 254, 346
7. Kalyanasundaram, K.; Grätzel, M. Coord. Chem. Rev. 1998, 77, 347
8. Lowry, M. S.; Bernhard, S. Chem.-Eur. J. 2006, 12, 7970
9. Ulbricht, C.; Beyer, B.; Friebe, C.; Winter, A.; Schubert, U. S. Adv. Mater. 2009, 21, 4418
10. Lalevée, J.; Blanchard, N.; Tehfe, M.-A.; Morlet-Savary, F.; Fouassier, J. P. Macromolecules 2010, 43, 10191
11. Lalevée, J.; Peter, M.; Dumur, F.; Gigmes, D.; Blanchard, N.; Tehfe, M.-A.; Morlet-Savary, F.; Fouassier, J. P. Chem.-Eur. J. 2011, 17, 15027
12. Fors, B. P.; Hawker, C. J. Angew. Chem., Int. Ed. 2012, 51, 8850
13. Howerton, B. S.; Heidary, D. K.; Glazer, E. C. J. Am. Chem. Soc. 2012, 134, 8324
14. Renaud, P.; Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2001.
15. Curran, D. P. Synthesis 1988, 1988, 417
16. Curran, D. P. Synthesis 1988, 1988, 489
17. Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886
18. Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77
19. Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756
20. Ischay, M. A.; Yoon, T. P. Eur. J. Org. Chem. 2012, 3359
21. Zeitler, K. Angew. Chem., Int. Ed. 2009, 48, 9785
22. Yoon, T. P.; Ischay, M. A.; Du, J. Nature Chem. 2010, 2, 527
23. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102
24. Teply, F. Collect. Czech. Chem. Commun. 2011, 76, 859
25. Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828
26. Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687
27. Wallentin, C.-J.; Nguyen, J. D.; Stephenson, C. R. J. Chimia 2012, 66, 394
28. Fagnoni, M.; Dondi, D.; Ravelli, D.; Albini, A. Chem. Rev. 2007, 107, 2725
29. Pandey, G. Top. Curr. Chem. 1993, 168, 175
30. Miranda, M. A.; García, H. Chem. Rev. 1994, 94, 1063
31. Fukuzumi, S.; Ohkubo, K. Chem. Sci. 2013, 4, 561
32. Wang, Y.; Wang, X.; Antonietti, M. Angew. Chem., Int. Ed. 2012, 51, 68
33. Kisch, H. Angew. Chem., Int. Ed. 2013, 52, 812
34. Campagna, S.; Puntoriero, F.; Nastasi, F.; Bergamini, G.; Balzani, V. Top. Curr. Chem. 2007, 280, 117
35. McCusker, J. K. Acc. Chem. Res. 2003, 36, 876
36. Bock, C. R.; Connor, J. A.; Gutierrez, A. R.; Meyer, T. J.; Whitten, D. G.; Sullivan, B. P.; Nagle, J. K. J. Am. Chem. Soc. 1979, 101, 4815
37. Throughout this Review, redox potentials are quoted against the saturated calomel electrode (SCE). In some cases, the referenced potentials have been determined versus different electrodes and have been converted to SCE for the purpose of comparison. For conversion constants, see: Pavlishchuk, V. V.; Addison, A. W. Inorg. Chim. Acta 2000, 298, 97
38. Tucker, J. W.; Stephenson, C. R. J. J. Org. Chem. 2012, 77, 1617
39. Turro, N. J. Modern Molecular Photochemistry; Benjamin/Cummings: Menlo Park, CA, 1978.
40. Pac, C.; Ihama, M.; Yasuda, M.; Miyauchi, Y.; Sakurai, H. J. Am. Chem. Soc. 1981, 103, 6495
41. Tanner, D. D.; Kharrat, A.; Oumar-Mahamat, H. Can. J. Chem. 1990, 68, 1662
42. Pac, C.; Miyauchi, Y.; Ishitani, O.; Ihama, M.; Yasuda, M.; Sakurai, H. J. Org. Chem. 1984, 49, 26
43. Ishitani, O.; Ihama, M.; Miyauchi, Y.; Pac, C. J. Chem. Soc., Perkin Trans. 1 1985, 1527
44. Ishitani, O.; Pac, C.; Sakurai, H. J. Org. Chem. 1983, 48, 2941
45. Ishitani, O.; Yanagida, S.; Takamuku, S.; Pac, C. J. Org. Chem. 1987, 52, 2790
46. Fukuzumi, S.; Mochizuki, S.; Tanaka, T. J. Phys. Chem. 1990, 94, 722
47. Fukuzumi, S.; Koumitsu, S.; Hironaka, K.; Tanaka, T. J. Am. Chem. Soc. 1987, 109, 305
48. Tanner, D. D.; Singh, H. K. J. Org. Chem. 1986, 51, 5182
49. Hironaka, K.; Fukuzumi, S.; Tanaka, T. J. Chem. Soc., Perkin Trans. 2 1984, 1705
50. Kern, J.-M.; Sauvage, J.-P. J. Chem. Soc., Chem. Commun. 1987, 546
51. Lawless, J. G.; Bartak, D. E.; Hawley, M. D. J. Am. Chem. Soc. 1969, 91, 7121
52. Wayner, D. D. M.; Dannenberg, J. J.; Griller, D. Chem. Phys. Lett. 1986, 131, 189
53. Dinnocenzo, J. P.; Banach, T. E. J. Am. Chem. Soc. 1989, 111, 8646
54. Nguyen, J. D.; D'Amato, E. M.; Narayanam, J. M. R.; Stephenson, C. R. J. Nature Chem. 2012, 4, 854
55. Flamigni, L.; Barbieri, A.; Sabatini, C.; Ventura, B.; Barigelletti, F. Top. Curr. Chem. 2007, 281, 143
56. Howes, K. R.; Bakac, A.; Espenson, J. H. Inorg. Chem. 1988, 27, 3147
57. This reaction has been applied to the development of a one-pot deoxygenation of alcohols: Nguyen, J. D.; Reiß, B.; Dai, C.; Stephenson, C. R. J. Chem. Commun. 2013, ASAP, DOI: 10.1039/C2CC37206A.
58. Goren, Z.; Willner, I. J. Am. Chem. Soc. 1983, 105, 7764
59. Maidan, R.; Goren, Z.; Becker, J. Y.; Willner, I. J. Am. Chem. Soc. 1984, 106, 6217
60. Willner, I.; Goren, Z.; Mandler, D.; Maidan, R.; Degani, Y. J. Photochem. 1985, 28, 215
61. Bockman, T. M.; Kochi, J. K. J. Org. Chem. 1990, 55, 4127
62. Willner, I.; Tsfania, T.; Eichen, Y. J. Org. Chem. 1990, 55, 2656
63. Maji, T.; Karmakar, A.; Reiser, O. J. Org. Chem. 2011, 76, 736
64. The merger of photoredox and viologen catalysis has also been applied to the reduction of carbonyls: Herance, J. R.; Ferrer, B.; Bourdelande, J. L.; Marquet, J.; Garcia, H. Chem.-Eur. J. 2006, 12, 3890
65. Maidan, R.; Willner, I. J. Am. Chem. Soc. 1986, 108, 1080
66. Mandler, D.; Willner, I. J. Am. Chem. Soc. 1984, 106, 5352
67. Mandler, D.; Willner, I. J. Chem. Soc., Perkin Trans. 2 1986, 805
68. Mandler, D.; Willner, I. J. Chem. Soc., Chem. Commun. 1986, 851
69. Hedstrand, D. M.; Kruizinga, W. M.; Kellogg, R. M. Tetrahedron Lett. 1978, 19, 1255
70. van Bergen, T. J.; Hedstrand, D. M.; Kruizinga, W. H.; Kellogg, R. M. J. Org. Chem. 1979, 44, 4953
71. Zhu, X.-Q.; Li, H.-R.; Li, Q.; Ai, T.; Lu, J.-Y.; Yang, Y.; Cheng, J.-P. Chem.-Eur. J. 2003, 9, 871
72. Nakamura, K.; Fujii, M.; Mekata, H.; Oka, S.; Ohno, A. Chem. Lett. 1986, 87
73. Hirao, T.; Shiori, J.; Okahata, N. Bull. Chem. Soc. Jpn. 2004, 77, 1763
74. Gazi, S.; Ananthakrishnan, R. Appl. Catal., B 2011, 105, 317
75. Chen, Y.; Kamlet, A. S.; Steinman, J. B.; Liu, D. R. Nat. Chem. 2011, 3, 146
76. Willner, I.; Ford, W. E.; Otvos, J. W.; Calvin, M. Nature 1979, 280, 823
77. Zhu, M.; Zheng, N. Synthesis 2011, 14, 2223
78. Crutchley, R. J.; Lever, A. B. P. J. Am. Chem. Soc. 1980, 102, 7128
79. Haga, M.-A.; Dodsworth, E. S.; Eryavec, G.; Seymour, P.; Lever, A. B. P. Inorg. Chem. 1985, 24, 1901
80. Photoredox catalysis has also been employed to reduce nitroalkenes to oximes: Tomioka, H.; Ueda, K.; Ohi, H.; Izawa, Y. Chem. Lett. 1986, 1359
81. Tucker, J. W.; Nguyen, J. D.; Narayanam, J. M. R.; Krabbe, S. W.; Stephenson, C. R. J. Chem. Commun. 2010, 46, 4985
82. 6: 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
83. For another report on this reaction type: Kim, H.; Lee, C. Angew. Chem., Int. Ed. 2012, 51, 12303
84. Tucker, J. W.; Stephenson, C. R. J. Org. Lett. 2011, 13, 5468
85. Larraufie, M.-H.; Pellet, R.; Fensterbank, L.; Goddard, J.-P.; Lacoîte, E.; Malacria, M.; Ollivier, C. Angew. Chem., Int. Ed. 2011, 50, 4463
86. 2+ and dimethylbenzimidazoles as stoichiometric reductants: Hasegawa, E.; Takizawa, S.; Seida, T.; Yamaguchi, A.; Yamaguchi, N.; Chiba, N.; Takahashi, T.; Ikeda, H.; Akiyama, K. Tetrahedron 2006, 62, 6581
87. Guindon, Y.; Jung, G.; Guérin, B.; Ogilvie, W. W. Synlett 1998, 213
88. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449
89. Okada, K.; Okamoto, K.; Morita, N.; Okubo, K.; Oda, M. J. Am. Chem. Soc. 1991, 113, 9401
90. Okada, K.; Okubo, K.; Morita, N.; Oda, M. Chem. Lett. 1993, 2021
91. Okada, K.; Okubo, K.; Morita, N.; Oda, M. Tetrahedron Lett. 1992, 33, 7377
92. Edson, J. B.; Spencer, L. P.; Boncella, J. M. Org. Lett. 2011, 13, 6156
93. Sundararajan, C.; Falvey, D. E. J. Am. Chem. Soc. 2005, 127, 8000
94. Borak, J. B.; Falvey, D. E. J. Org. Chem. 2009, 74, 3894
95. Boncella and co-workers have exploited this photoredox deprotection protocol to achieve in situ vesicle formation upon cleavage of long-chain N -methylpicolinium esters: DeClue, M. S.; Monnard, P.-A.; Bailey, J. A.; Maurer, S. E.; Collis, G. E.; Ziock, H.-J.; Rasmussen, S.; Boncella, J. M. J. Am. Chem. Soc. 2009, 131, 931
96. Zlotorzynska, M.; Sammis, G. M. Org. Lett. 2011, 13, 6264
97. Cano-Yelo, H.; Deronzier, A. Tetrahedron Lett. 1984, 25, 5517
98. Allongue, P.; Delamar, M.; Desbat, B.; Fagebaume, O.; Hitmi, R.; Pinson, J.; Savéant, J.-M. J. Am. Chem. Soc. 1997, 119, 201
99. Galli, C. Chem. Rev. 1988, 88, 765
100. Su, Y.; Zhang, L.; Jiao, N. Org. Lett. 2011, 13, 2168
101. Recupero, F.; Punta, C. Chem. Rev. 2007, 107, 3800
102. Zou, Y.-Q.; Chen, J.-R.; Liu, X.-P.; Lu, L.-Q.; Davis, R. L.; Jørgensen, K. A.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 784
103. Cheng, Y.; Yang, J.; Qu, Y.; Li, P. Org. Lett. 2012, 14, 98
104. Conrad, J. C.; Kong, J.; Laforteza, B. N.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 11640
105. Inamoto, K.; Hasegawa, C.; Hiroya, K.; Doi, T. Org. Lett. 2008, 10, 5147
106. Joyce, L. L.; Batey, R. A. Org. Lett. 2009, 11, 2792
107. Inamoto, K.; Hasegawa, C.; Kawasaki, J.; Hiroya, K.; Doi, T. Adv. Synth. Catal. 2010, 352, 2643
108. Tucker, J. W.; Narayanam, J. M. R.; Shah, P. S.; Stephenson, C. R. J. Chem. Commun. 2011, 47, 5040
109. Lowry, M. S.; Goldsmith, J. I.; Slinker, J. D.; Rohl, R.; Pascal, R. A.; Malliaras, G. G.; Bernhard, S. Chem. Mater. 2005, 17, 5712
110. Murayama, E.; Kohda, A.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1980, 947
111. Lechner, R.; König, B. Synthesis 2010, 1712
112. Bauer, E. B. Chem. Soc. Rev. 2012, 41, 3153
113. Herrero, S.; Usón, M. A. J. Chem. Educ. 1995, 72, 1065
114. Hamada, T.; Ishida, H.; Usui, S.; Watanabe, Y.; Tsumura, K.; Ohkubo, K. J. Chem. Soc., Chem. Commun. 1993, 909
115. Hamada, T.; Ishida, H.; Usui, S.; Tsumura, K.; Ohkubo, K. J. Mol. Catal. 1994, 88, L1
116. Fancy, D. A.; Kodadek, T. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 6020
117. Kim, K.; Fancy, D. A.; Carney, D.; Kodadek, T. J. Am. Chem. Soc. 1999, 121, 11896
118. Fancy, D. A.; Denison, C.; Kim, K.; Xie, Y.; Holdeman, T.; Amini, F.; Kodadek, T. Chem. Biol. 2000, 7, 697
119. Amini, F.; Denison, C.; Lin, H.-J.; Kuo, L.; Kodadek, T. Chem. Biol. 2003, 10, 1115
120. Denison, C.; Kodadek, T. J. Proteome Res. 2004, 3, 417
121. Kodadek, T.; Duroux-Richard, I.; Bonnafous, J.-C. Trends Pharmacol. Sci. 2005, 26, 210
122. Parker, V. D.; Tilset, M. J. Am. Chem. Soc. 1991, 113, 8778
123. Condie, A. G.; González-Gómez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2010, 132, 1464
124. Vicinal diamines have also been employed as substrates in photoredox aza-Henry reactions; iminium generation occurs upon C-C bond cleavage of the amine radical cation: Cai, S.; Zhao, X.; Wang, X.; Liu, Q.; Li, Z.; Wang, D. Z. Angew. Chem., Int. Ed. 2012, 51, 8050
125. Rueping, M.; Zhu, S.; Koenigs, R. M. Chem. Commun. 2011, 47, 12709
126. Zhao, G.; Yang, C.; Guo, L.; Sun, H.; Chen, C.; Xia, W. Chem. Commun. 2012, 48, 2337
127. Rueping, M.; Vila, C.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C. Chem. Commun. 2011, 47, 2360
128. Rueping, M.; Zhu, S.; Koenigs, R. M. Chem. Commun. 2011, 47, 8679
129. Freeman, D. B.; Furst, L.; Condie, A. G.; Stephenson, C. R. J. Org. Lett. 2012, 14, 94
130. Wang, Z.-Q.; Hu, M.; Huang, X.-C.; Gong, L.-B.; Xie, Y.-X.; Li, J.-H. J. Org. Chem. 2012, 77, 8705
131. Zhu, S.; Rueping, M. Chem. Commun. 2012, 48, 11960
132. Rueping, M.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C.; Leonori, D.; Vila, C. Chem.-Eur. J. 2012, 18, 5170
133. Pan, Y.; Wang, S.; Kee, C. W.; Dubuisson, E.; Yang, Y.; Loh, K. P.; Tan, C.-H. Green Chem. 2011, 13, 3341
134. Fu, W.; Guo, W.; Zou, G.; Xu, C. J. Fluorine Chem. 2012, 140, 88
135. Hari, D. P.; König, B. Org. Lett. 2011, 13, 3852
136. Pan, Y.; Kee, C. W.; Chen, L.; Tan, C.-H. Green Chem. 2011, 13, 2682
137. Liu, Q.; Li, Y.-N.; Zhang, H.-H.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Chem.-Eur. J. 2012, 18, 620
138. Mitkina, T.; Stanglmair, C.; Setzer, W.; Gruber, M.; Kisch, H.; König, B. Org. Biomol. Chem. 2012, 10, 3556
139. Xuan, J.; Cheng, Y.; An, J.; Lu, L.-Q.; Zhang, X.-X.; Xiao, W.-J. Chem. Commun. 2011, 47, 8337
140. Xuan, J.; Feng, Z.-J.; Duan, S.-W.; Xiao, W.-J. RSC Adv. 2012, 2, 4065
141. Hall, L. R.; Iwamoto, R. T.; Hanzlik, R. P. J. Org. Chem. 1989, 54, 2446
142. Seo, E. T.; Nelson, R. F.; Fritsch, J. M.; Marcoux, L. S.; Leedy, D. W.; Adams, R. N. J. Am. Chem. Soc. 1966, 88, 3498
143. Dai, C.; Meschini, F.; Narayanam, J. M. R.; Stephenson, C. R. J. J. Org. Chem. 2012, 77, 4425
144. DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094
145. 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
146. Rueping, M.; Leonori, D.; Poisson, T. Chem. Commun. 2011, 47, 9615
147. Maity, S.; Zheng, N. Angew. Chem., Int. Ed. 2012, 51, 9562
148. Cyclization rates of aminium radical cations are known to be significantly greater than those of the corresponding deprotonated aminyl radicals, see Table 4 of: Horner, J. H.; Musa, O. M.; Bouvier, A.; Newcomb, M. J. Am. Chem. Soc. 1998, 120, 7738
149. Curran, D. P. Synthesis 1988, 7, 489
150. Clark, A. J. Chem. Soc. Rev. 2002, 31, 1
151. Pintauer, T.; Matyjaszewski, K. Chem. Soc. Rev. 2008, 37, 1087
152. Barton, D. H. R.; Csiba, M. A.; Jaszberenyi, J. C. Tetrahedron Lett. 1994, 35, 2869
153. Nguyen, J. D.; Tucker, J. W.; Konieczynska, M. D.; Stephenson, C. R. J. J. Am. Chem. Soc. 2011, 133, 4160
154. Wallentin, C.-J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. J. Am. Chem. Soc. 2012, 134, 8875
155. Wayner, D. D. M.; Houmam, A. Acta Chem. Scand. 1998, 52, 377
156. Pirtsch, M.; Paria, S.; Matsuno, T.; Isobe, H.; Reiser, O. Chem.-Eur. J. 2012, 18, 7336
157. For the synthesis of trifluoromethyl alkenes via an ATRA pathway: Iqbal, N.; Choi, S.; Kim, E.; Cho, E. J. J. Org. Chem. 2012, 77, 11383
158. MacMillan, D. W. C. Nature 2008, 455, 304
159. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471
160. Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875
161. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
162. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
163. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359
164. Bonesi, S. M.; Erra-Balsells, R. J. Chem. Soc., Perkin Trans. 2 2000, 1583
165. Shih, H.-W.; Vander Wal, M. N.; Grange, R. L.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 13600
166. Neumann, M.; Füldner, S.; König, B.; Zeitler, K. Angew. Chem., Int. Ed. 2011, 50, 951
167. Cherevatskaya, M.; Neumann, M.; Füldner, S.; Harlander, C.; Kümmel, S.; Dankesreiter, S.; Pfitzner, A.; Zeitler, K.; König, B. Angew. Chem., Int. Ed. 2012, 51, 4062
168. Cano-Yelo, H.; Deronzier, A. J. Chem. Soc., Perkin Trans. 2 1984, 1093
169. Cano-Yelo, H.; Deronzier, A. J. Photochem. 1987, 37, 315
170. Hari, D. P.; Schroll, P.; König, B. J. Am. Chem. Soc. 2012, 134, 2958
171. Meerwein, H.; Büchner, E.; van Emster, K. J. Prakt. Chem. 1939, 152, 237
172. Kochi, J. K. J. Am. Chem. Soc. 1957, 79, 2942
173. Wetzel, A.; Pratsch, G.; Kolb, R.; Heinrich, M. R. Chem.-Eur. J. 2010, 16, 2547
174. Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18566
175. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
176. Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330
177. Deprez, N. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 11234
178. Tucker, J. W.; Narayanam, J. M. R.; Krabbe, S. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 368
179. Furst, L.; Matsuura, B. S.; Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 3104
180. Furst, L.; Narayanam, J. M. R.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2011, 50, 9655
181. Ju, X.; Liang, Y.; Jia, P.; Li, W.; Yu, W. Org. Biomol. Chem. 2012, 10, 498
182. Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224
183. Young, R. C.; Meyer, T. J.; Whitten, D. G. J. Am. Chem. Soc. 1976, 98, 286
184. Iqbal, N.; Choi, S.; Ko, E.; Cho, E. J. Tetrahedron Lett. 2012, 53, 2005
185. Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034
186. Chu, L.; Qing, F.-L. Org. Lett. 2010, 12, 5060
187. Senecal, T. D.; Parsons, A. T.; Buchwald, S. L. J. Org. Chem. 2011, 76, 1174
188. Jiang, X.; Chu, L.; Qing, F.-L. J. Org. Chem. 2012, 77, 1251
189. Xu, J.; Luo, D.-F.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Fu, Y.; Liu, L. Chem. Commun. 2011, 47, 4300
190. Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342
191. Rao, H.; Wang, P.; Li, C.-J. Eur. J. Org. Chem. 2012, 6503
192. Photoredox catalysis has also been applied to the 3-sulfenylation of N -methylindoles: Chen, M.; Huang, Z.-T.; Zheng, Q.-Y. Chem. Commun. 2012, 48, 11686
193. Schroll, P.; Hari, D. P.; König, B. ChemistryOpen 2012, 1, 130
194. Hering, T.; Hari, D. P.; König, B. J. Org. Chem. 2012, 77, 10347
195. Eosin Y has been employed in a synthesis of benzothiophenes from o -methylthio-arenediazonium salts and alkynes: Hari, D. P.; Hering, T.; König, B. Org. Lett. 2012, 14, 5334
196. Pham, P. V.; Nagib, D. A.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2011, 50, 6119
197. Cho, D. W.; Lee, H.-Y.; Oh, S. W.; Choi, J. H.; Park, H. J.; Mariano, P. S.; Yoon, U. C. J. Org. Chem. 2008, 73, 4539
198. Fukuzumi, S.; Fujita, M. J. Org. Chem. 1993, 58, 5405
199. Fukuzumi, S.; Fujita, M.; Matsubayashi, G.; Otera, J. Chem. Lett. 1993, 1451
200. Fujita, M.; Fukuzumi, S.; Matsubayashi, G.; Otera, J. Bull. Chem. Soc. Jpn. 1996, 69, 1107
201. Yasu, Y.; Koike, T.; Akita, M. Angew. Chem., Int. Ed. 2012, 51, 9567
202. Courant, T.; Masson, G. Chem.-Eur. J. 2012, 18, 423
203. For another report on the alkylation of enamides and enecarbamates: Jiang, H.; Huang, C.; Guo, J.; Zeng, C.; Zhang, Y.; Yu, S. Chem.-Eur. J. 2012, 18, 15158
204. Um, J. M.; Gutierrez, O.; Schoenebeck, F.; Houk, K. N.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 6001
205. Narasaka, K.; Okauchi, T.; Tanaka, K.; Murakami, M. Chem. Lett. 1992, 2099
206. Beeson, T. D.; Mastracchio, A.; Hong, J.-B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582
207. Yasu, Y.; Koike, T.; Akita, M. Chem. Commun. 2012, 48, 5355
208. Koike, T.; Akita, M. Chem. Lett. 2009, 38, 166
209. Liu, H.; Feng, W.; Kee, C. W.; Zhao, Y.; Leow, D.; Pan, Y.; Tan, C.-H. Green Chem. 2010, 12, 953
210. Yoon, H.-S.; Ho, X.-H.; Jang, J.; Lee, H.-J.; Kim, S.-J.; Jang, H.-Y. Org. Lett. 2012, 14, 3272
211. Koike, T.; Yasu, Y.; Akita, M. Chem. Lett. 2012, 41, 999
212. Baik, T.-G.; Luis, A. L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 6716
213. Wang, L.-C.; Jang, H.-Y.; Roh, Y.; Lynch, V.; Schultz, A. J.; Wang, X.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448
214. Roh, Y.; Jang, H.-Y.; Lynch, V.; Bauld, N. L.; Krische, M. J. Org. Lett. 2002, 4, 611
215. Yang, J.; Felton, G. A. N.; Bauld, N. L.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 1634
216. Yang, J.; Cauble, D. F.; Berro, A. J.; Bauld, N. L.; Krische, M. J. J. Org. Chem. 2004, 69, 7979
217. Felton, G. A. N.; Bauld, N. L. Tetrahedron Lett. 2004, 45, 8465
218. Felton, G. A. N.; Bauld, N. L. Tetrahedron 2004, 60, 10999
219. Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2009, 131, 14604
220. Tyson, E. L.; Farney, E. P.; Yoon, T. P. Org. Lett. 2012, 14, 1110
221. Du, J.; Espelt, L. R.; Guzei, I. A.; Yoon, T. P. Chem. Sci. 2011, 2, 2115
222. Pandey, G.; Hajra, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 1169
223. Pandey, G.; Hajra, S.; Ghorai, M. K.; Kumar, K. R. J. Am. Chem. Soc. 1997, 119, 8777
224. Zhao, G.; Yang, C.; Guo, L.; Sun, H.; Lin, R.; Xia, W. J. Org. Chem. 2012, 77, 6302
225. Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, R. A., Jr.; Reynolds, D. W.; Wirth, D. D.; Chiou, H.-S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371
226. Bauld, N. L. Tetrahedron 1989, 45, 5307
227. Ischay, M. A.; Lu, Z.; Yoon, T. P. J. Am. Chem. Soc. 2010, 132, 8572
228. Yueh, W.; Bauld, N. L. J. Phys. Org. Chem. 1996, 9, 529
229. Ischay, M. A.; Ament, M. S.; Yoon, T. P. Chem. Sci. 2012, 3, 2807
230. Hunziker, M.; Ludi, A. J. Am. Chem. Soc. 1977, 99, 7370
231. Rillema, D. P.; Allen, G.; Meyer, T. J.; Conrad, D. Inorg. Chem. 1983, 22, 1617
232. Hurtley, A. E.; Cismesia, M. A.; Ischay, M. A.; Yoon, T. P. Tetrahedron 2011, 67, 4442
233. Lin, S.; Ischay, M. A.; Fry, C. G.; Yoon, T. P. J. Am. Chem. Soc. 2011, 133, 19350
234. Lin, S.; Padilla, C. E.; Ischay, M. A.; Yoon, T. P. Tetrahedron Lett. 2012, 53, 3073
235. Parrish, J. D.; Ischay, M. A.; Lu, Z.; Guo, S.; Peters, N. R.; Yoon, T. P. Org. Lett. 2012, 14, 1640
236. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317
237. Lu, Z.; Shen, M.; Yoon, T. P. J. Am. Chem. Soc. 2011, 133, 1162
238. Norin, T. Acta Chem. Scand. 1965, 19, 1289
239. Dauben, W. G.; Deviny, E. J. J. Org. Chem. 1966, 31, 3794
240. Tanko, J. M.; Drumright, R. E. J. Am. Chem. Soc. 1990, 112, 5362
241. Maity, S.; Zhu, M.; Shinabery, R. S.; Zheng, N. Angew. Chem., Int. Ed. 2012, 51, 222
242. Chow, Y. L.; Danen, W. C.; Nelsen, S. F.; Rosenblatt, D. H. Chem. Rev. 1978, 78, 243
243. Renaud, P.; Giraud, L. Synthesis 1996, 913
244. Kohls, P.; Jadhav, D.; Pandey, G.; Reiser, O. Org. Lett. 2012, 14, 672
245. Miyake, Y.; Nakajima, K.; Nishibayashi, Y. J. Am. Chem. Soc. 2012, 134, 3338
246. Miyake, Y.; Ashida, Y.; Nakajima, K.; Nishibayashi, Y. Chem. Commun. 2012, 48, 6966
247. Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233
248. Xu, W.; Jeon, Y. T.; Hasegawa, E.; Yoon, U. C.; Mariano, P. S. J. Am. Chem. Soc. 1989, 111, 406
249. Jeon, Y. T.; Lee, C.-P.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 8847
250. Xu, W.; Zhang, X.-M.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 8863
251. Albini, A.; Mella, M.; Freccero, M. Tetrahedron 1994, 50, 575
252. Andrews, R. S.; Becker, J. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2010, 49, 7274
253. Andrews, R. S.; Becker, J. J.; Gagné, M. R. Org. Lett. 2011, 13, 2406
254. Giese, B.; Dupuis, J. Angew. Chem., Int. Ed. Engl. 1983, 22, 622
255. Adlington, R. M.; Baldwin, J. E.; Basak, A.; Kozyrod, R. P. J. Chem. Soc., Chem. Commun. 1983, 944
256. Rondinini, S. B.; Mussini, P. R.; Crippa, F.; Sello, G. Electrochem. Commun. 2000, 2, 491
257. Gilbert, B. C.; Trenwith, M.; Dobbs, A. J. J. Chem. Soc., Perkin Trans. 2 1974, 1772
258. Malatesta, V.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 609
259. Giese, B.; Dupuis, J. Tetrahedron Lett. 1984, 25, 1349
260. Dupuis, J.; Giese, B.; Rüegge, D.; Fischer, H.; Korth, H.-G.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 896
261. Giese, B.; Dupuis, J.; Haßkerl, T.; Meixner, J. Tetrahedron Lett. 1983, 24, 703
262. Schnermann, M. J.; Overman, L. E. Angew. Chem., Int. Ed. 2012, 51, 9576
263. McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114
264. Ohashi, M.; Miyake, K. Chem. Lett. 1977, 615
265. Ohashi, M.; Miyake, K.; Tsujimoto, K. Bull. Chem. Soc. Jpn. 1980, 53, 1683
266. Yamada, S.; Nakagawa, Y.; Watabiki, O.; Suzuki, S.; Ohashi, M. Chem. Lett. 1986, 361
267. Hasegawa, E.; Brumfield, M. A.; Mariano, P. S. J. Org. Chem. 1988, 53, 5435
268. Wakasa, M.; Sakaguchi, Y.; Nakamura, J.; Hayashi, H. J. Phys. Chem. 1992, 96, 9651
269. Tyson, E. L.; Ament, M. S.; Yoon, T. P. J. Org. Chem. 2012, ASAP. DOI: 10.1021/jo3020825.
270. Bordwell, F. G.; Zhang, X.-M.; Satish, A. V.; Cheng, J.-P. J. Am. Chem. Soc. 1994, 116, 6605
271. Hydroetherification reactions have also been achieved using organic visible light photocatalysis: Hamilton, D. S.; Nicewicz, D. A. J. Am. Chem. Soc. 2012, 134, 18577
272. Dai, C.; Narayanam, J. M. R.; Stephenson, C. R. J. Nat. Chem. 2011, 3, 140
273. Konieczynska, M. D.; Dai, C.; Stephenson, C. R. J. Org. Biomol. Chem. 2012, 10, 4509
274. Ikezawa, H.; Kutal, C.; Yasufuku, K.; Yamazaki, H. J. Am. Chem. Soc. 1986, 108, 1589
275. Wrighton, M.; Markham, J. J. Phys. Chem. 1973, 77, 3042
276. Islangulov, R. R.; Castellano, F. N. Angew. Chem., Int. Ed. 2006, 45, 5957
277. Lu, Z.; Yoon, T. P. Angew. Chem., Int. Ed. 2012, 51, 10329
278. Ni, T.; Caldwell, R. A.; Melton, L. A. J. Am. Chem. Soc. 1989, 111, 457
279. An energy transfer pathway has also been employed to achieve the [2 + 2] cycloaddition of 3-ylideneoxindoles: Zou, Y.-Q.; Duan, S.-W.; Meng, X.-G.; Hu, X.-G.; Gao, S.; Chen, J.-R.; Xiao, W.-J. Tetrahedron 2012, 68, 6914
280. Inagaki, A.; Akita, M. Coord. Chem. Rev. 2010, 254, 1220
281. Osawa, M.; Hoshino, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 2001, 40, 3472
282. Inagaki, A.; Edure, S.; Yatsuda, S.; Akita, M. Chem. Commun. 2005, 5468
283. Inagaki, A.; Yatsuda, S.; Edure, S.; Suzuki, A.; Takahashi, T.; Akita, M. Inorg. Chem. 2007, 46, 2432
284. Inagaki, A.; Nakagawa, H.; Akita, M.; Inoue, K.; Sakai, M.; Fujii, M. Dalton Trans. 2008, 6709
285. Murata, K.; Ito, M.; Inagaki, A.; Akita, M. Chem. Lett. 2010, 39, 915
286. Nitadori, H.; Takahashi, T.; Inagaki, A.; Akita, M. Inorg. Chem. 2012, 51, 51
287. 2+ has also been proposed to accelerate a Sonogashira reaction via energy transfer: Osawa, M.; Nagai, H.; Akita, M. Dalton Trans. 2007, 827
288. Andrews, R. S.; Becker, J. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2012, 51, 4140
289. Tucker, J. W.; Zhang, Y.; Jamison, T. F.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2012, 51, 4144
290. Neumann, M.; Zeitler, K. Org. Lett. 2012, 14, 2658
291. Bou-Hamdan, F. R.; Seeberger, P. H. Chem. Sci. 2012, 3, 1612