Electron and hydrogen transfer in organic photochemical reactions

Journal of Physical Organic Chemistry

Volumn 28, Issue 2, 2015, Pages 121-136

  Hoffmann, Norbert ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Heterogeneous photocatalysis; Homogeneous photocatalysis; Hydrogen abstraction; Photochemical electron transfer; Radical ions; Radical reactions; Stereo and regioselectivity; , Unsaturated carbonyl compounds Copyright

Indexed keywords

CARBONYL COMPOUNDS; CATALYSIS; CHEMICAL ACTIVATION; CHEMICAL COMPOUNDS; COPYRIGHTS; ELECTRON TRANSITIONS; ELECTRONS; FREE RADICAL REACTIONS; HYDROGEN; PHOTOCATALYSIS; PROTONS; REACTION KINETICS; UNSATURATED COMPOUNDS;

HETEROGENEOUS PHOTOCATALYSIS; HYDROGEN ABSTRACTION; PHOTOCHEMICAL ELECTRON TRANSFER; RADICAL IONS; RADICAL REACTIONS; UNSATURATED CARBONYL COMPOUNDS;

PHOTOCHEMICAL REACTIONS;

EID: 84922926813     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.3370     Document Type: Review

References (268)

1. P. Klán, J. Wirz, Photochemistry of Organic Compounds, Wiley, Chichester, 2009.
2. N. J. Turro, V. Ramamurthy, J. C. Scaiano, Modern Molecular Photochemistry of Organic Molecules, University Science Books, Sausalito, 2010.
3. a) N. J. Turro, Angew. Chem. Int. Ed. 1986, 25, 882-892
4. b) M. Olivucci, F. Santoro, Angew. Chem. Int. Ed. 2008, 47, 6322-6325
5. c) I. Schapiro, F. Melaccio, E. N. Laricheva, M. Olivucci, Photochem. Photobiol. Sci. 2011, 10, 867-886
6. d) H. E. Zimmerman, Angew. Chem. Int. Ed. 1969, 8, 1-11.
7. a) N. Hoffmann, Chem. Rev., 2008, 108, 1052-1103
8. b) T. Bach, J. P. Hehn, Angew. Chem. Int. Ed. 2011, 50, 1000-1045
9. c) C.-L. Ciana, C. G. Bochet, Chimia 2007, 61, 650-654.
10. a) A. Griesbeck, M. Oelgemöller, F. Ghetti, Eds., CRC Handbook of Organic Photochemistry and Photobiology, 3rd Edition, CRC Press, Boca Raton, 2012
11. b) A. Albini, M. Fagnoni, Eds., Handbook of Synthetic Photochemistry, Wiley-VCH, Weinheim, 2010
12. c) A. G. Griesbeck, J. Mattay, Eds., Synthetic Organic Photochemistry; Marcel Dekker, New York, 2005.
13. a) A. Albini, M. Fagnoni, Green Chem. 2004, 6, 1-6
14. b) M. Oelgemöller, C. Jung, J. Mattay, Pure Appl. Chem. 2007, 79, 1939-1947
15. c) S. Protti, D. Dondi, M. Fagnoni, A. Albini, Green Chem. 2009, 11, 239-249.
16. M. Oelgemöller, J. Chin. Chem. Soc. 2014, 61, 743-748.
17. N. Hoffmann, Photochem. Photobiol. Sci. 2012, 11, 1613-1641.
18. a) E. E. Coyle, M. Oelgemöller, Photochem. Photobiol. Sci. 2008, 7, 1313-1322
19. b) T. Fukuyama, M. T. Rahman, M. Sato, I. Ryu, Synlett 2008, 2008, 151-163
20. c) M. Oelgemöller, O. Shvydkiv, Molecules 2011, 16, 7522-7550
21. d) J. P. Knowles, L. D. Elliott, K. I. Booker-Milburn, Beilstein J. Org. Chem. 2012, 8, 2025-2052
22. e) M. Oelgemöller, N. Hoffmann, O. Shvydkiv, Aust. J. Chem. 2014, 67, 337-342.
23. a) G. J. Kavarnos, Fundamentals of Photoinduced Electron Transfer, VCH Publishers Inc., New York, 1993
24. b) J. Mattay, Angew. Chem. Int. Ed. 1987, 26, 825-845
25. c) M. Julliard, M. Chanon, Chem. Rev. 1983, 83, 425-506.
26. V. Balzani, Ed., Electron Transfer in Chemistry, Vol. 1-5, Wiley-VCH, Weinheim, 2001.
27. K.-L. Han, G.-J. Zhao, Eds., Hydrogen Bonding and Transfer in the Excited State, Volumes 1, 2, Wiley, Chichester, 2011.
28. a) R. A. Marcus, Ann. Rev. Phys. Chem. 1964, 15, 155-196
29. b) R. A. Marcus, Angew. Chem. Int. Ed. 1993, 32, 1111-1121.
30. a) R. A. Marcus, J. Phys. Chem. 1968, 72, 891-899
31. b) R. A. Marcus, Faraday Discuss. Chem. Soc. 1982, 74, 7-15.
32. a) M. T. M. Koper, Chem. Sci. 2013, 4, 2710-2723
33. b) J. Bonin, C. Costentin, M. Robert, J.-M. Savéant, C. Tard, Acc. Chem. Res. 2012, 45, 372-381
34. c) C. Li, D. Danovich, S. Shaik, Chem. Sci. 2012, 3, 1903-1918
35. d) J. M. Mayer, I. J. Rhile, F. B. Larsen, E. A. Mader, T. F. Markle, A. G. DiPasquale, Photosynth. Res. 2006, 87, 3-20
36. e) J. Stubbe, D. G. Nocera, C. S. Yee, M. C. Y. Chang, Chem. Rev. 2003, 103, 2167-2201.
37. a) A. Migliore, N. F. Polizzi, M. J. Therien, D. N. Beratan, Chem. Rev. 2014, 114, 3381-3465
38. b) J. P. Layfield, S. Hammes-Schiffer, Chem. Rev. 2014, 114, 3466-3494
39. c) J. Bonin, M. Robert, Photochem. Photobiol. 2011, 87, 1190-1203.
40. M.-H. V. Huynh, T. J. Meyer, Chem. Rev. 2007, 107, 5004-5064.
41. a) C. T. Saouma, J. M. Mayer, Chem. Sci. 2014, 5, 21-31
42. b) J. M. Hodgkiss, J. Rosenthal, D. G. Nocera, In Hydrogen-Transfer Reactions, Volumes 1-4 (Eds: J. T. Hynes, J. P. Klinman, H.-H. Limbach, R. L. Schowen), Wiley-VCH, Weinheim, 2007, 503-562.
43. J. Fossey, D. Lefort, J. Sorba, Free Radicals in Organic Chemistry, Wiley, Chichester, 1995.
44. D. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996.
45. a) P. Renaud, M. P. Sibi, Eds., Radicals in Organic Synthesis, Vol. 1 and 2, Wiley-VCH, Weinheim, 2001
46. b) C. Chatgilialoglu, A. Studer, Eds., Encyclopedia of Radicals in Chemistry, Biology and Materials, Wiley, Chichester, 2012.
47. a) H. Fischer, L. Radom, Angew. Chem. Int. Ed. 2001, 40, 1340-1371
48. b) M. L. Poutsma, J. Phys. Org. Chem. 2008, 21, 758-782.
49. N. Hoffmann, S. Bertrand, S. Marinković, J. Pesch, Pure Appl. Chem. 2006, 78, 2227-2246.
50. A. G. Griesbeck, N. Hoffmann, K. D. Warzecha, Acc. Chem. Res. 2007, 40, 128-140.
51. a) S. Bertrand, C. Glapski, N. Hoffmann, J.-P. Pete, Tetrahedron Lett. 1999, 40, 3169-3172
52. b) S. Bertrand, N. Hoffmann, J.-P. Pete, Tetrahedron Lett. 1999, 40, 3173-3174
53. c) S. Bertrand, N. Hoffmann, J.-P. Pete, Eur. J. Org. Chem. 2000, 2000, 2227-2238.
54. N. Hoffmann, H. Görner, Chem. Phys. Lett. 2004, 383, 451-455.
55. For structure and properties of α-amino alkyl radicals, see: a) F. D. Lewis, Acc. Chem. Res. 1986, 19, 401-405
56. b) G. W. Dombrowski, J. P. Dinnocenzo, S. Farid, J. L. Goodman, I. R. Gould, J. Org. Chem. 1999, 64, 427-431
57. c) D. D. M. Wayner, K. B. Clark, A. Rauk, D. Yu, D. A. Amstrong, J. Am. Chem. Soc. 1997, 119, 8925-8932
58. d) J. Lalevée, X. Allonas, J.-P. Fouassier, J. Am. Chem. Soc. 2002, 124, 9613-9621
59. e) J. Lalevée, X. Allonas, J.-P. Fouassier, J. Phys. Chem. A 2004, 108, 4326-4334
60. f) J. Lalevée, X. Allonas, J.-P. Fouassier, J. Org. Chem. 2005, 70, 814-819
61. g) J. Lalevée, X. Allonas, J.-P. Fouassier, J. Phys. Chem. A 2007, 111, 6991-6998.
62. a) D. Harakat, J. Pesch, S. Marinković, N. Hoffmann, Org. Biomol. Chem. 2006, 4, 1202-1205
63. b) A. Gassama, C. Ernenwein, N. Hoffmann, ChemSusChem 2009, 2, 1130-1137.
64. A. Bauer, F. Westkämper, S. Grimme, T. Bach, Nature 2005, 436, 1139-1140.
65. a) N. Hoffmann, J. Photochem. Photobiol. C: Photochem Rev. 2008, 9, 43-60
66. b) G. Pandey, Synlett 1992, 1992, 546-552; See also:
67. c) M. Fagnoni, D. Dondi, D. Ravelli, A. Albini, Chem. Rev. 2007, 107, 2725-2756.
68. a) S. Marinković, N. Hoffmann, Chem. Commun. 2001, 37, 1576-1578
69. b) S. Marinković, N. Hoffmann, Intern. J. Photoenergy 2003, 5, 175-182.
70. For recent examples of similar reactions with amines: a)M. Rueping, C. Vila, R. M. Koenigs, K. Poscharny, D. C. Fabry, Chem. Commun. 2011, 47, 2360-2362
71. b) M. Rueping, J. Zoller, D. C. Fabry, K. Poscharny, R. M. Koenigs, T. E. Weirich, J. Mayer, Chem. Eur. J. 2012, 18, 3478-3481
72. c) P. Kohls, D. Jadhav, G. Pandey, O. Reiser, Org. Lett. 2012, 14, 672-675
73. d) Y. Miyake, Y. Ashida, K. Nakajima, Y. Nishibayashi, Chem. Commun. 2012, 48, 6966-6968
74. e) Y. Miyake, K. Nakajima, Y. Nishibayashi, J. Am. Chem. Soc. 2012, 134, 3338-3341
75. f) Y. Miyake, Y. Ashida, K. Nakajima, Y. Nishibayashi, Chem. Eur. J. 2014, 20, 6120-6125
76. g) A. McNally, C. P. Prier, D. W. C. MacMillan, Science 2011, 334, 1114-1117.
77. L. Shi, W. Xia, Chem. Soc. Rev. 2012, 41, 7687-7697.
78. For reviews on photoredox catalysis with visible light: a) F. Teplý, Collect. Czech. Chem. Commun. 2011, 76, 859-917
79. b) M. Reckenthäler, A. G. Griesbeck, Adv. Synth. Catal. 2013, 355, 2727-2744
80. c) T. P. Yoon, M. A. Ischay, J. Du, Nat. Chem. 2010, 2, 527-532
81. d) J. M. R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev. 2011, 40, 102-113
82. e) J. Xuan, W.-J. Xiao, Angew. Chem. Int. Ed. 2012, 51, 6828-6838
83. f) C. R. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113, 5322-5363
84. g) D. P. Hari, B. König, Chem. Commun. 2014, 50, 6688-6699
85. h) B. König, Ed., Chemical Photocatalysis, De Gruyter, Berlin, 2013
86. i) T. Koike, M. Akita, Synlett 2013, 24, 2492-2505
87. j) J. Hu, J. Wang, T. H. Nguyen, N. Zheng, Beilstein J. Org. Chem. 2013, 9, 1977-2001
88. k) N. Hoffmann, ChemSusChem 2012, 5, 352-371
89. l) K. Zeidler, Angew. Chem. Int. Ed. 2009, 48, 9785-9789
90. m) P. Renaud, P. Leong, Science 2008, 322, 55-56
91. n) K. Fidaly, C. Ceballos, A. Falguières, M. S.-I. Veitia, A. Guy, C. Ferroud, Green Chem. 2012, 14, 1293-1297.
92. a) S. Bertrand, N. Hoffmann, J.-P. Pete, V. Bulach, Chem. Commun. 1999, 35, 2291-2292
93. b) S. Bertrand, N. Hoffmann, S. Humbel, J. P. Pete, J. Org. Chem. 2000, 65, 8690-8703.
94. S. Marinković, N. Hoffmann, Eur. J. Org Chem. 2004, 2004, 3102-3107.
95. a) J.-M. Herrmann, Top. Catal. 2005, 34, 49-65
96. b) M. R. Hoffmann, S. T. Martin, W. Choi, D. W. Bahnemann, Chem. Rev. 1995, 95, 69-96
97. c) O. Legrini, E. Oliveros, A. M. Braun, Chem. Rev. 1993, 93, 671-698
98. d) J. Lyu, L. Zhu, C. Burda, Catal. Today 2014, 225, 24-33
99. e) P. Pischat Ed., Photocatalysis and Water Purification, Wiley-VCH, Weinheim, 2013
100. f) S. Lacombe, T.-H. Tran-Thi, C. Guillard, J.-M. Herrmann, V. Keller-Spitzer, N. Keller, M.-T. Maurette, P. Pischat, T. Pigot, C. Pulgarin, A.-G. Rincon, D. Robert, Actual. Chim. 2007, 308-309, 79-93
101. g) T. Ochiai, A. Fujishima, J. Photochem. Photobiol. C 2012, 13, 247-262.
102. a) H. Kisch, Angew. Chem. Int. Ed. 2013, 52, 812-847
103. b) M.-A. Fox, M. T. Dulay, Chem. Rev. 1993, 93, 341-357
104. c) G. Palmisano, E. García-López, G. Marcí, V. Loddo, S. Yurdakal, V. Augugliaro, L. Palmisano, Chem. Commun. 2010, 46, 7047-7089.
105. a) D. W. Manley, R. T. McBurney, P. Miller, R. F. Howe, S. Rhydderch, J. C. Walton, J. Am. Chem. Soc. 2012, 134, 13580-13583
106. b) D. W. Manley, R. T. McBurney, P. Miller, J. C. Walton, A. Mills, C. O'Rourke, J. Org. Chem. 2014, 79, 1386-1398.
107. D. W. Manley, A. Mills, C. O'Rourke, A. M. Z. Slawin, J. C. Walton, Chem. Eur. J. 2014, 20, 5492-5500.
108. X.-M. Zhang, P. Mariano, J. Org. Chem. 1991, 56, 1655-1660.
109. D. Rehm, A. Weller, Isr. J. Chem. 1970, 8, 259-271.
110. A. Rosspeintner, D. R. Kattnig, G. Angulo, S. Landgraf, G. Grampp, Chem. Eur. J. 2008, 14, 6213-6221.
111. Z. V. Todres, Ion-Radical Organic Chemistry, 2nd Edition, CRC Press Taylor & Francis Group, LLC Boca Raton, 2009.
112. R. Jahjah, A. Gassama, F. Dumur, S. Marinković, S. Richert, S. Landgraf, A. Lebrun, C. Cadiou, P. Sellès, N. Hoffmann, J. Org. Chem. 2011, 76, 7104-7118.
113. a) R. Taylor, Electrophilic Aromatic Substitution, Wiley, Chichester, 1990
114. b) R. Taylor, Chimia 1968, 22, 1-64.
115. L. Strekowski, M. Hojjat, S. E. Patterson, A. S. Kiselyov, J. Heterocycl. Chem. 1994, 31, 1413-1419.
116. a) M. Periasamy, N. KishoreBabu, K. N. Jayakumar, Tetrahedron Lett. 2003, 44, 8939-8941; See also:
117. b) W. A. Moradi, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7996-8002.
118. a) R. M. Bowman, T. R. Chamberlain, C.-W. Huang, J. J. McCullough, J. Am. Chem. Soc. 1974, 96, 692-700
119. b) D. Mangion, M. Frizzle, D. R. Arnold, T. S. Cameron, Synthesis 2001, 2001, 1215-1222.
120. M. Ohashi, Y. Tanaka, S. Yamada, Tetrahedron Lett. 1977, 18, 3629-3632.
121. F. Müller, J. Mattay, Chem. Rev. 1993, 93, 99-117.
122. S. Barata-Vallejo, M. M. Flesia, B. Lantaño, J. E. Argüello, A. Peñéñory, A. Postigo, Eur. J. Org. Chem. 2013, 2013, 998-1008.
123. B. Lantaño, S. Barata-Vallejo, M. R. Torviso, S. M. Bonesi, J. E. Argüello, A. Postigo, J. Fluorine Chem. 2014, 161, 149-155.
124. A. Studer, D. P. Curran, Angew. Chem. Int. Ed. 2011, 50, 5018-5022.
125. For further examples, see: a)C. Karapire, S. Icli, In CRC Handbook of Organic Photochemistry and Photobiology, 2nd Edition (Eds. W. Horspool, F. Lenci), CRC Press Boca Raton, 2004, 37/1-37/14
126. b) Q.-Y. Chen, Z.-T. Li, J. Chem. Soc. Perkin Trans. 1 1992, 1443-1445
127. c) Q.-Y. Chen, Z.-T. Li, J. Chem. Soc. Perkin Trans. 1 1993, 1705-1710
128. d) Q.-Y. Chen, Z.-T. Li, J. Org. Chem. 1993, 58, 2599-2604.
129. B. Sezen, D. Sames, In Handbook of C-H Transformations, Vol. 1 (Ed: G. Dyker), Wiley-VCH, Weinheim, 2005, 3-10.
130. a) P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Wiley-VCH, Weinheim, 2004
131. b) H. Amii, A. Nagaki, J. Yoshida, Beistein J. Org. Chem. 2013, 9, 2793-2802
132. c) J.-P. Bégué, D. Bonnet-Delpon, Bioorganic and Medicinal Chemistry of Fluorine, Wiley, Hoboken, 2008
133. d) V. Gouverneur, K. Müller, Eds., Fluorine in Pharmaceutical and Medicinal Chemistry: From Biophysical Aspects to Clinical Applications, World Scientific Publishing Company, London, 2012
134. e) K. Uneyama, Organofluorine Chemistry, Blackwell Publishing, Oxford, 2006
135. f) A. Studer, Angew. Chem. Int. Ed. 2012, 51, 8950-8958
136. g) D. Yu. Mikhaylov, Yu. H. Budnikova, Rus. Chem. Rev. 2013, 82, 835-864
137. h) W. R. Dolbier, Jr., Chem. Rev. 1996, 96, 1557-1584
138. i) S. Barata-Vallejo, A. Postigo, Eur. J. Org. Chem. 2012, 2012, 1889-1899
139. j) A. Postigo, Can. J. Chem. 2012, 90, 493-497.
140. For some examples with aromatic compounds, see: a) S. Murakami, H. Ishii, T. Tajima, T. Fuchigami, Tetrahedron 2006, 62, 3761-3769
141. b) N. J. W. Straathof, H. P. L. Gemoets, X. Wang, J. C. Schouten, V. Hessel, T. Noël, ChemSusChem 2014, 7, 1612-1671
142. c) Y. Ye, M. S. Sanford, J. Am. Chem. Soc. 2012, 134, 9034-9037
143. d) V. N. Boiko, Beilstein J. Org. Chem. 2010, 6, 880-921
144. e) M. Iisuka, M. Yoshida, J. Fluorine Chem. 2009, 130, 926-932
145. f) S. P. Pitre, C. D. McTiernan, H. Ismaili, J. C. Scaiano, ACS Catal. 2014, 4, 2530-2535
146. g) D. A. Nagib, D. W. C. MacMillan, Nature 2011, 480, 224-228.
147. U. C. Yoon, P. S. Mariano, Acc. Chem. Res. 1992, 25, 233-240.
148. a) W. Xu, Y. T. Jeon, E. Hasegawa, U. C. Yoon, P. S. Mariano, J. Am. Chem. Soc. 1989, 111, 406-408
149. b) W. Xu, X.-M. Zhang, P. S. Mariano, J. Am. Chem. Soc. 1991, 113, 8863-8878.
150. a) K. Fuji, Chem. Rev. 1993, 93, 2037-2066
151. b) J. Christoffers, A. Mann, Angew. Chem. Int. Ed. 2001, 40, 4591-4597
152. c) J. Christoffers, A. Baro, Adv. Synth. Catal. 2005, 347, 1473-1482
153. d) J. Christoffers, A. Baro, Eds., Quaternary Stereocenters, Wiley-VCH, Weinheim, 2005.
154. a) N. J. Pienta, J. E. McKimmey, J. Am. Chem. Soc. 1982, 104, 5501-5502
155. b) N. Pienta, J. Am. Chem. Soc. 1982, 104, 5501-5502
156. c) D. Smith, N. Pienta, Tetrahedron Lett. 1984, 25, 915-918
157. d) R. C. Cookson, J. Hudec, N. A. Mirza, Chem. Commun. 1968, 4, 180-180
158. e) D. I. Schuster, R. Bonneau, D. A. Dunn, J. M. Rao, J. Joussot-Dubien, J. Am. Chem. Soc. 1984, 106, 2706-2707
159. f) D. A. Dunn, D. I. Schuster, R. Bonneau, J. Am. Chem. Soc. 1985, 107, 2802-2804
160. g) D. Weir, J. C. Scaiano, D. I. Schuster, Can. J. Chem. 1988, 66, 2595-2600.
161. a) U.-C. Yoon, J.-U. Kim, E. Hasegawa, P. S. Mariano, J. Am. Chem. Soc. 1987, 109, 4421-4423
162. b) Y. T. Jeon, C.-P. Lee, P. S. Mariano, J. Am. Chem. Soc. 1991, 113, 8847-8863.
163. E. Hasegawa, W. Xu, P. S. Mariano, U.-C. Yoon, J.-U. Kim, J. Am. Chem. Soc. 1988, 110, 8099-8111.
164. a) U. C. Yoon, P. S. Mariano, R. S. Givens, B. W. Atwater III, Adv. Electron Transfer Chem. 1994, 4, 117-205
165. b) F. D. Lewis, Adv. Electron Transfer Chem. 1996, 5, 1-39.
166. a) A. G. Griesbeck, W. Kramer, M. Oelgemöller, Synlett 1999, 1999, 1169-1178
167. b) M. Oelgemöller, A. G. Griesbeck, J. Photochem. Photobiol. C 2002, 3, 109-127
168. c) G. McDermott, D. J. Yoo, M. Oelgemöller, Heterocycles 2005, 65, 2221-2257
169. d) U. C. Yoon, P. S. Mariano, Acc. Chem. Res. 2001, 34, 523-533
170. e) M. Horvat, K. Mlinarić-Majerski, N. Basarić, Croat. Chem. Acta 2010, 83, 179-188.
171. M. Oelgemöller, W. H. Kramer, J. Photochem. Photobiol. C 2010, 11, 210-244.
172. See for example: a) S. Hu, D. C. Neckers, Tetrahedon 1997, 53, 7165-7180
173. b) S. Hu, D. C. Neckers, J. Org. Chem. 1997, 62, 7827-7831.
174. R. Jahjah, A. Gassama, V. Bulach, C. Suzuki, M. Abe, N. Hoffmann, A. Martinez, J.-M. Nuzillard, Chem. Eur. J. 2010, 16, 3341-3354.
175. a) R. Bonneau, J. Am. Chem. Soc. 1980, 102, 3816-3822
176. b) S. Yamauchi, N. Hirota, J. Higuchi, J. Phys. Chem. 1988, 92, 2129-2133
177. c) D. I. Schuster, D. A. Dunn, G. E. Heibel, P. B. Brown, J. M. Rao, J. Woning, R. Bonneau, J. Am. Chem. Soc. 1991, 113, 6245-6255
178. d) M. Reguero, M. Olivucci, F. Bernardi, M. A. Robb, J. Am. Chem. Soc. 1994, 116, 2103-2114
179. e) S. Wilsey, L. González, M. A. Robb, K. N. Houk, J. Am. Chem. Soc. 2000, 122, 5866-5876.
180. a) N. Hoffmann, H. Buschmann, G. Raabe, H.-D. Scharf, Tetrahedron 1994, 50, 11167-11186
181. b) K. Wiesner, Tetrahedron 1975, 31, 1655-1658
182. c) G. Marini-Bettòlo, S. P. Sahoo, G. A. Poulton, T. Y. R. Tsai, K. Wiesner, Tetrahedron 1980, 36, 719-721
183. d) N. Braussaud, N. Hoffmann, H.-D. Scharf, Tetrahedron 1997, 53, 14701-14712
184. e) D. Becker, M. Nagler, Y. Sahali, N. Haddad, J. Org. Chem. 1991, 56, 4537-4543.
185. a) R. Alibés, J. L. Bourdelande, J. Font, A. Gregori, T. Parella, Tetrahedron 1996, 52, 1267-1278; See also:
186. b) P. de March, M. Figueredo, J. Font, J. Raya, A. Alvarez-Larena, J. F. Piniella, J. Org. Chem. 2003, 68, 2437-2447.
187. K. Hayday, R. D. McKelvey, J. Org. Chem. 1976, 41, 2222-2223.
188. a) R. U. Lemieux, Pure Appl. Chem. 1975, 25, 527-548
189. b) P. Delongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon Press, Oxford, 1983
190. c) E. Juaristi, G. Cuevas, The Anomeric Effect, CRC Press, Boca Raton, 1995.
191. a) B. Giese, Angew. Chem. Int. Ed. 1989, 28, 969-980
192. b) A. L. J. Beckwith, D. Crich, P. J. Duggan, Q. Yao, Chem. Rev. 1997, 97, 3273-3312
193. c) H. Abe, M. Terauchi, A. Matsuda, S. Shuto, J. Org. Chem. 2003, 68, 7439-7447
194. d) H. Abe, S. Shuto, A. Matsuda, J. Am. Chem. Soc. 2001, 123, 11870-11882
195. e) J. C. López, A. M. Gómez, B. Fraser-Reid, J. Org. Chem. 1995, 60, 3871-3878.
196. Y.-R. Luo, Comprehensive Handbook of Chemical Bond Energies, CRC Press, Boca Raton, 2007.
197. K.-D. Ginzel, E. Steckhan, D. Degner, Tetrahedron 1987, 43, 5797-5805.
198. M. Mella, E. Fasani, A. Alibini, J. Org. Chem. 1992, 57, 3051-3057.
199. a) H. Zipse, Top. Curr. Chem. 2006, 263, 163-189
200. b) J. Hioe, H. Zipse, In Encyclopedia of Radicals in Chemistry, Biology and Materials, Vol. 1 (Eds. C. Chatgilialoglu, A. Studer), Wiley, Chichester, 2012, 449-475.
201. a) M. Mella, M. Freccero, A. Albini, J. Org. Chem. 1994, 59, 1047-1052
202. b) M. Mella, M. Fagnoni, M. Freccero, E. Fasani, A. Albini, Chem. Soc. Rev. 1998, 27, 81-89.
203. D. Brown, M. G. B. Drew, J. Mann, J. Chem. Soc. Perkin Trans. 1 1997, 3651-3656.
204. H. Graalfs, R. Fröhlich, C. Wolff, J. Mattay, Eur. J. Org. Chem. 1999, 1999, 1057-1073.
205. R. F. Borkman, D. R. Kearns, J. Chem. Phys. 1966, 44, 945-949.
206. W. J. Leigh, D. R. Arnold, J. Chem. Soc. Chem. Commun. 1980, 16, 406-408.
207. N. W. A. Geraghty, M. T. Lohan, In CRC Handbook of Organic Photochemistry and Photobiology, 3rd Edition (Eds. A. Griesbeck, M. Oelgemöller, F. Ghetti), CRC Press, Boca Raton, 2012, 445-488.
208. For some examples, see: a)N. Hoffmann, Tetrahedron Asymmetry 1994, 5, 879-886
209. b) S. Aida, Y. Nishiyama, K. Kakiuchi, N. Hoffmann, A. Fon, M. Oelgemöller, Rapid Commun. Photosci. 2013, 2, 68-71.
210. A. Amougay, J.-P. Pete, O. Piva, Bull. Soc. Chem. Fr. 1996, 133, 625-635.
211. C. Meyer, O. Piva, J.-P. Pete, Tetrahedron Lett. 1996, 37, 5885-5888.
212. a) R. Reinfried, D. Belluš, K. Schaffner, Helv. Chim. Acta 1971, 54, 1517-1531
213. b) D. I. Schuster, P. B. Brown, L. J. Capponi, C. A. Rhodes, J. C. Scaiano, P. C. Tucker, D. Weir, J. Am. Chem. Soc. 1987, 109, 2533-2534.
214. a) A. C. Chan, D. I. Schuster, J. Am. Chem. Soc. 1986, 108, 4561-4567
215. b) D. Belluš, D. R. Kearns, K. Schaffner, Helv. Chim. Acta 1969, 52, 971-1009
216. c) D. Belluš, K. Schaffner, Helv. Chim. Acta 1969, 52, 1010-1015
217. d) P. de Mayo, Acc. Chem. Res. 1971, 4, 41-47
218. e) D. I. Schuster, M. M. Greenberg, I. M. Nuñez, P. C. Tucker, J. Org. Chem. 1983, 48, 2615-2619
219. f) D. I. Schuster, G. Lem, N. A. Kaprinidis, Chem. Rev. 1993, 93, 3-22
220. g) D. I. Schuster, In The Chemistry of Enones, Part 2 (Eds: S. Patai, Z. Rappoport), Wiley, Chichester, 1989, 623-756.
221. S. Le Blanc, J.-P. Pete, O. Piva, Tetrahedron Lett. 1992, 33, 1993-1996.
222. a) A. Amougay, O. Piva, J.-P. Pete, Tetrahedron Lett. 1993, 34, 5285-5286
223. b) A. Amougay, O. Letsch, J.-P. Pete, O. Piva, Tetrahedron 1996, 52, 2405-2420.
224. F. Toda, H. Miyamoto, K. Takeda, R. Matsugawa, N. Maruyama, J. Org. Chem. 1993, 58, 6208-6211.
225. For some reviews, see: a) M. Sakamoto, Chem. Eur. J. 1997, 3, 684-689
226. b) C. Yang, W. Xia, Chem. Asian J. 2009, 4, 1774-1784
227. c) J. R. Scheffer, In Chiral Photochemistry (Eds., Y. Inoue, V. Ramamurthy), Marcel Dekker, New York, 2004, 463-483.
228. a) L. A. Paquette, P. D. Pansegrau, P. E. Wiedeman, J. P. Springer, J. Org. Chem. 1988, 53, 1461-1466
229. b) S. Wolff, W. L. Schreiber, A. B. Smith III, W. C. Agosta, J. Am. Chem. Soc. 1972, 94, 7797-7806
230. c) W. Herz, V. S. Iyer, M. G. Nair, J. Saltiel, J. Am. Chem. Soc. 1977, 99, 2704-2713
231. d) Y. Tobe, T. Iseki, K. Kakiuchi, Y. Odaira, Tetrahedron Lett. 1984, 25, 3895-3896
232. e) D. Brown, C. D. Cardin, J. Mann, J. Chem. Soc., Chem. Commun. 1995, 31, 825-826
233. f) T. Kobayashi, M. Kurono, H. Sato, K. Nakanishi, J. Am. Chem. Soc. 1972, 94, 2863-2865
234. g) F. Nobs, U. Burger, K. Schaffner, Helv. Chim. Acta 1977, 60, 1607-1628
235. h) J. A. Turner, V. Iyer, R. S. McEwen, W. Herz, J. Org. Chem. 1974, 39, 117-119
236. i) D. H. R. Barton, P. D. Magnus, J. I. Okogun, J. Chem. Soc. Perkin Trans. I 1972, 1103-1105
237. j) B. Gioia, A. Marchesini, G. D. Andreetti, G. Bocelli, P. Sgarabotto, J. Chem. Soc. Perkin Trans. I 1977, 410-415
238. k) T. Hasegawa, W. Watabe, H. Aoyama, Y. Omote, Tetrahedron 1977, 33, 485-488
239. l) A. B. Smith III, A. M. Foster, W. C. Agosta, J. Am. Chem. Soc. 1972, 94, 5100-5101
240. m) S. Kohmoto, T. Kreher, Y. Miyaji, M. Yamamoto, K. Yamada, J. Org. Chem. 1992, 57, 3490-3492.
241. a) P. J. Wagner, In CRC Handbook of Organic Photochemistry and Photobiology, 2nd Edition (Eds: W. Horspool, F. Lenci), CRC Press, Boca Raton, 2004, 58/1-58/70
242. b) P. Wessig, In CRC Handbook of Organic Photochemistry and Photobiology, 2nd Edition (Eds. W. Horspool, F. Lenci), CRC Press, Boca Raton, 2004, 57/1-57/20.
243. a) A. G. Griesbeck, Synlett 2003, 2003, 451-472
244. b) P. J. Wagner, Acc. Chem. Res. 1989, 22, 83-91.
245. V. Ramamurthy, A. Natarajan, L. S. Kaanumalle, S. Karthikeyan, J. Sivaguru, J. Shailaja, A. Joy, In Chiral Photochemistry (Eds: Y. Inoue, V. Ramamurthy), Marcel Dekker, New York, 2004, 563-631.
246. R. Breslow, Acc. Chem. Res. 1980, 13, 170-177.
247. a) R. Breslow, S. Baldwin, T. Flechtner, P. Kalicky, S. Liu, W. Washburn, J. Am. Chem. Soc. 1973, 95, 3251-3262
248. b) R. L. Wife, D. Prezant, R. Breslow, Tetrahedron Lett. 1976, 17, 517-520.
249. M. E. Jung, T. W. Johnson, J. Am. Chem. Soc. 1997, 119, 12412-12413.
250. P. B. Rees, Steroids 2001, 66, 481-497.
251. For some recent examples, see: H. Gong, J. R. Williams, Org. Lett. 2006, 8, 2253-2255 and references cited therein.
252. a) M. A. Winnik, R. E. Trueman, G. Jackowski, D. S. Saunders, S. G. Whittington, J. Am. Chem. Soc. 1974, 96, 4843-4848
253. b) M. A. Winnik, C. K. Lee, S. Basu, D. S. Saunders, J. Am. Chem. Soc. 1974, 96, 6182-6184.
254. a) G.-C. Wang, M. A. Winnik, H. J. Schäfer, W. Schmidt, Chin. Sci. Bull. 1993, 38, 615-616; See also:
255. b) M. A. Winnik, G.-C. Wang, H. J. Schäfer, W. Schmidt, J. Photochem. 1986, 34, 281-287.
256. H. Tamiaki, A. Kiyomori, K. Maruyama, Bull. Chem. Soc. Jpn. 1993, 66, 1768-1772.
257. a) A. Herrera, M. Rondón, E. Suárez, Synlett 2007, 2007, 1851-1856
258. b) A. Herrera, M. Rondón, E. Suárez, J. Org. Chem. 2008, 73, 3384-3391.
259. a) D. Alvarez-Dorta, E. I. Leon, A. R. Kennedy, C. Riesco-Fagundo, E. Suárez, Angew. Chem. Int. Ed. 2008, 47, 8917-8919
260. b) D. Alvarez-Dorta, E. I. León, A. R. Kennedy, A. Martín, I. Pérez-Martín, C. Riesco-Fagundo, E. Suárez, Chem. Eur. J. 2014, 20, 2663-2671.
261. a) M. Abe, Chem. Rev. 2013, 113, 7011-7088.
262. b) M. Abe, J. Ye, M. Mishima, Chem. Soc. Rev. 2012, 41, 3808-3820.
263. a) L. Salem, C. Rowland, Angew. Chem. Int. Ed. 1972, 11, 92-111
264. b) J. Michl, J. Am. Chem. Soc. 1996, 118, 3568-3579
265. c) L. Carlacci, C. Doubleday, Jr., T. R. Furlani, H. F. King, J. W. McIver, Jr. J. Am. Chem. Soc. 1987, 109, 5323-5329.
266. a) A. G. Griesbeck, H. Mauder, S. Stadtmüller, Acc. Chem. Res. 1994, 27, 70-75
267. b) A. G. Griesbeck, M. Abe, S. Bondock, Acc. Chem. Res. 2004, 37, 919-928
268. c) A. G. Kutateladze, J. Am. Chem. Soc. 2001, 123, 9279-9282.