Photoinduced electron transfer reactions in heterocyclic chemistry

Heterocycles

Volumn 60, Issue 8, 2003, Pages 1921-1958

  Fagnoni, Maurizio ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; HYDROGEN;

ADDITION REACTION; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CYCLOADDITION; ELECTRON TRANSPORT; FRAGMENTATION REACTION; LIGHT; OXYGENATION; REDUCTION; REVIEW; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0041967245     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-03-566     Document Type: Review

References (150)

1. M. Chanon, M. D. Hawley, and M. A. Fox, in Photoinduced Electron Transfer, ed. by M. A. Fox and M. Chanon, Part A, Elsevier, Amsterdam, 1988, pp. 1-59.
2. A. Alberti, P. Carloni, L. Eberson, L. Greci, and P. Stipa, J. Chem. Soc., Perkin Trans. 2, 1997, 887.
3. K. Mizuno, M. Ishii, and Y. Otsuji, J. Am. Chem. Soc., 1981, 103, 5570.
4. J. M. Bobbitt, C. L. Kulkarni, and J. Willis, Heterocycles, 1981, 15, 495.
5. Measured in 0.51 M aq. NaOH; S. Viraraghavan, Bull. Chem. Soc. Jpn., 1992, 65, 1101.
6. R. J. Enemaerke, T. B. Christensen, H. Jensen, and K. Daasbjerg, J. Chem. Soc., Perkin Trans. 2, 2001, 1620.
7. C. Thobie-Gautier and C. Degrand, J. Org. Chem., 1991, 56, 5703.
8. M. Genesty, G. Pommatau, and C. Degrand, Acta Chem. Scand., 1999, 53, 952.
9. J. Ouyang and A. J. Bard, J. Phys. Chem., 1987, 91, 4058.
10. For a review on the use of pyrylium salts see: M. A. Miranda and H. Garcia, Chem. Rev., 1994, 94, 1063.
11. For the reduction potentials reported in Scheme 4 see: M. Chanon and L. Eberson, in Photoinduced Electron Transfer, ed. by M. A. Fox and M. Chanon, Part A, Elsevier, Amsterdam, 1988, pp. 409-597.
12. Phthalimides are probably the most worthnoting substrates belonging to this category. Their PET reactions are reviewed elsewhere; see U. C. Yoon and P. S. Mariano, Acc. Chem. Res., 2001, 34, 523.
13. (a) A. Albini and M. Fagnoni, in Electron Transfer in Chemistry, Vol. 2, ed. by V. Balzani, Wiley-VCH, 2001, 338.
14. (b) A. Lablache-Combier, in ref. 1 Part. A, pp. 134-312.
15. A. Albini, M. Mella, and M. Freccero, Tetrahedron, 1994, 50, 575.
16. (a) W. Carruthers, in Cycloaddition Reactions in Organic Synthesis Pergamon Press 1990.
17. (b) F. Mueller and J. Mattay, Chem. Rev., 1993, 93, 99.
18. For a detailed description of cation radical cycloadditions reactions see N. L. Bauld, Tetrahedron, 1989, 45, 5307.
19. J. Mattay, Angew. Chem., Int. Ed. Engl., 1987, 26, 825.
20. T. Wirth and S. Blechert, Tetrahedron Lett., 1992, 33, 6621.
21. (a) A. Gieseler, E. Steckhan, and O. Wiest, Synlett, 1990, 275.
22. (b) A. Gieseler, E. Steckhan, O. Wiest, and F. Knoch, J. Org. Chem., 1991, 56, 1405.
23. G. C. Calhoun and G. B. Schuster, J. Am. Chem. Soc., 1986, 108, 8021.
24. O. Wiest, E. Steckhan, and F. Grein, J. Org. Chem., 1992, 57, 4034.
25. (a) T. Peglow, S. Blechert, and E. Steckhan, Chem. Comm., 1999, 433.
26. (b) U. Haberl, E. Steckhan, S. Blechert, and O. Wiest, Chem. Eur. J., 1999, 5, 2859.
27. (a) O. Wiest and E. Steckhan, Angew. Chem., Int. Ed. Engl., 1993, 32, 901.
28. (b) O. Wiest and E. Steckhan, Tetrahedron Lett., 1993, 34, 6391.
29. C. F. Guertler, E. Steckhan, and S. Blechert, J. Org. Chem., 1996, 61, 4136.
30. J. Botzem, U. Haberl, E. Steckhan, and S. Blechert, Acta Chem. Scand., 1998, 52, 175.
31. K. Mizuno, R. Kaji, H. Okada, and Y. Otsuji, J. Chem. Soc., Chem. Comm., 1978, 594.
32. (a) J. Guilford, II in Organic Photochemistry, ed. by A. Padwa, Vol 5, 1981, pp. 1-122.
33. (b) T. Bach, Synlett, 2000, 1699.
34. M. D'Auria, R. Racioppi, and G. Romaniello, Eur. J. Org. Chem., 2000, 3265.
35. J. Xue, Y. Zhang, T. Wu, H.-K. Fun, and J.-H. Xu, J. Chem. Soc., Perkin Trans. 1, 2001, 183.
36. M. M. Alam and O. Ito, Bull. Chem. Soc. Jpn., 1999, 72, 339.
37. R. A. Rossi, A. B. Pierini, and A. N. Santiago, Organic Reactions, 1999, 54, 1-271.
38. (a) J. K. Kim and J. F. Bunnett, J. Am. Chem. Soc., 1970, 92, 7463.
39. (b) R. A. Rossi and J. F. Bunnett, J. Org. Chem., 1973, 38, 1407.
40. (a) J. V. Hay and J. F. Wolfe, J. Am. Chem. Soc., 1975, 97, 3702.
41. J. V. Hay, T. Hudlicky, and J. F. Wolfe, J. Am. Chem. Soc., 1975, 97, 374.
42. (a) A. P. Komin and J. F. Wolfe, J. Org. Chem., 1977, 42, 2481.
43. (b) D. R. Carver, T. D. Greenwood, J. S. Hubbard, A. P. Komin, Y. P. Sachdeva, and J. F. Wolfe, J. Org. Chem., 1983, 48, 1180.
44. R. Beugelmans, B. Boudet, and L. Quintero, Tetrahedron Lett., 1980, 21, 1943.
45. (a) D. R. Carver, A. P. Komin, J. S. Hubbard, and J. F. Wolfe, J. Org. Chem., 1981, 46, 294.
46. (b) E. A. Oostven and H. C. van der Plas, Recl. Trav. Chim. Pay-Bas, 1979, 98, 441.
47. S. C. Dillender Jr., T. D. Greenwood, S. H. Mukta, and J. F. Wolfe, J. Org. Chem., 1986, 51, 1184.
48. L. Beltran, C. Galvez, M. Prats, and J. Salgado, J. Heterocycl. Chem., 1992, 29, 905.
49. M. P. Moon, A. P. Komin, and J. F. Wolfe, J. Org. Chem., 1983, 48, 2392.
50. (a) M. Novi, G. Garbarino, G. Petrillo, and C. Dell'Erba, J. Org. Chem., 1987, 52, 5382.
51. (b) R. A. Rossi and S. M. Palacios, J. Org. Chem., 1981, 46, 5300.
52. R. Beugelmans, M. Bois-Choussy, and B. Boudet, Tetrahedron, 1983, 39, 4153.
53. R. R. Goehring, Y. P. Sachdeva, J. S. Pisipati, M. C. Sleevi, and J. F. Wolfe, J. Am. Chem. Soc., 1985, 107, 435.
54. (a) S. Kyushin, Y. Nakadaira, and M. Ohashi, Chem. Lett., 1990, 2191.
55. (b) E. Baciocchi, G. Doddi, M. Ioele, and G. Ercolani, Tetrahedron, 1993, 49, 3793.
56. For a detailed description of the photoinduced electron transfer functionalization of the 10-methylacridinium ion see: N. Satoh and S. Fukuzumi in Reviews on Heteroatom Chemistry, Vol 20, pp. 249-281.
57. (a) S. Fukuzumi, S. Kuroda, and T. Tanaka, J. Chem. Soc., Chem. Comm., 1986, 1553.
58. (b) S. Fukuzumi, T. Kitano, and T. Tanaka, Chem. Lett., 1989, 1231.
59. (a) S. Fukuzumi, M. Fujita, and J. Otera, J. Chem. Soc., Chem. Comm., 1993, 1536.
60. (b) M. Fujita, A. Ishida, S. Takamuku, and S. Fukuzumi, J. Am. Chem. Soc., 1996, 118, 8566.
61. (a) S. Fukuzumi, T. Kitano, and K. Mochida, Chem. Lett., 1989, 2177.
62. (b) S. Fukuzumi, T. Kitano, and K. Mochida, J. Chem. Soc., Chem. Comm., 1990, 1236.
63. (c) S. Fukuzumi, K. Ohkubo, T. Suenobu, K. Kato, M. Fujitsuka, and O. Ito, J. Am. Chem. Soc., 2001, 123, 8459.
64. F. Minisci, F. Fontana, T. Caronna, and L. Zhao, Tetrahedron Lett., 1992, 33, 3201.
65. M. Fujita and S. Fukuzumi, J. Chem. Soc., Perkin Trans. 2, 1993, 1915.
66. U. C. Yoon, S. L. Quillen, and P. S. Mariano, Tetrahedron Lett., 1982, 23, 919.
67. R. Suau, F. Najera, and R. Rico, Tetrahedron, 1999, 55, 4019.
68. M. Schmittel, G. Viola, F. Dall'Acqua, and G. Morbach, Chem. Comm., 2003, 646.
69. D. Zhu and J. K. Kochi, Organometallics, 1999, 18, 161.
70. (a) C. Pac, A. Nakasone, and H. Sakurai, J. Am. Chem. Soc., 1977, 99, 5806.
71. (b) T. Majima, C. Pac, A. Nakasone, and H. Sakurai, J. Am. Chem. Soc., 1981, 103, 4499.
72. (a) P. Grandclaudon, A. Lablanche-Combier, and C. Parkanyi, Tetrahedron, 1973, 29, 651.
73. (b) P. Grandclaudon, and A. Lablanche-Combier, J. Chem. Soc., Chem. Comm., 1971, 892.
74. A. Buquet, A. Couture, A. Lablanche-Combier, and A. Pollet, Tetrahedron, 1981, 37, 75.
75. C. P. Butts, L. Eberson, R. Gonzalez-Luque, C. M. Hartshorn, M. P. Hartshorn, M. Merchan, W. T. Robinson, B. O. Roos, C. Vallance, and B. R. Wood, Acta Chem. Scand., 1997, 51, 984.
76. (a) T. Kubota and H. Sakurai, Chem. Lett., 1972, 923.
77. (b) T. Kubota and H. Sakurai, Chem. Lett., 1972, 1249.
78. J. J. McCullough, W. S. Wu, and C. W. Huang, J. Chem. Soc., Perkin Trans. 2, 1972, 370.
79. K. Yamasaki, T Matsuura, and I. Saito, J. Chem. Soc., Chem. Comm., 1974, 944.
80. (a) S. Naruto and O. Yonemitsu, Tetrahedron Lett., 1971, 2297.
81. (b) S. Naruto and O. Yonemitsu, Chem. Pharm. Bull., 1972, 20, 2163.
82. R. J. Sundberg, in Organic Photochemistry, Vol. 6, ed. by. A. Padwa, Marcel Dekker Inc. New York and Basel 1983, pp. 121.
83. R. J. Sundberg and J. D. Bloom, J. Org. Chem., 1980, 45, 3382.
84. (a) S. Naruto and O. Yonemitsu, Tetrahedron Lett., 1975, 3399.
85. (b) S. Naruto and O. Yonemitsu, Chem. Pharm. Bull., 1980, 28, 900.
86. (c) A. Wu and V. Snieckus, Tetrahedron Lett., 1975, 2057.
87. (d) R. J. Sundberg and F. X. Smith, J. Org. Chem., 1975, 40, 2613.
88. (e) R. J. Sundberg, J. G. Luis, R. L. Parton, S. Schreiber, P.C. Srinivasan, P. Lamb, P. Forcier, and R. F. Bryan, J. Org. Chem., 1978, 43, 4859.
89. (f) T. Kobayashi, T. F. Spande, H. Aoyagi, and B. Witkop, J. Med. Chem., 1969, 12, 636.
90. N. G. Anderson and R. G. Lawton, Tetrahedron Lett., 1977, 1843.
91. S. M. Bonesi and R. Erra-Balsells, An. Asoc. Quim. Argentina, 1999, 87, 127.
92. A. Gaplovsky, S. Toma, J.-L. Luche, B. Jakubikova, K. Gaplovska, and R. Mracnova, J. Chem. Soc., Perkin Trans. 2, 2002, 652.
93. Q.-Y. Chen and Z.-T. Li, J. Chem. Soc., Perkin Trans. 1, 1993, 645.
94. (a) K. Maruyama, T. Otsuki, and H. Tamiaki Bull. Chem. Soc. Jpn. 1985, 58, 3049.
95. (b) K. Maruyama and H. Tamiaki Bull. Chem. Soc. Jpn., 1987, 60, 3049.
96. (c) K. Maruyama and T. Otsuki, Chem. Lett., 1977, 851.
97. (d) K. Maruyama and T. Otsuki, Bull. Chem. Soc. Jpn., 1977, 50, 3429.
98. (a) Q.-Y. Chen and Z.-T. Li, J. Chem. Soc., Perkin Trans. 1, 1993, 1705.
99. (b) Q.-Y. Chen and Z.-T. Li, J. Org. Chem., 1993, 58, 2599.
100. C. P. Butts, L. Eberson, M. P. Hartshorn, F. Radner, and B. R. Wood, Acta Chem. Scand., 1997, 51, 476.
101. J. Xu, J. He, and Y. Qian, J. Chem. Soc., Chem. Comm., 1991, 714.
102. M. D'Auria, Tetrahedron, 1991, 47, 9225.
103. (a) G. A. Russell, D. Guo, W. Baik, and S. J. Herron, Heterocycles, 1989, 28, 143.
104. (b) G. A. Russell, R. Rajaratnam, L. Wang, B. Z. Shi, B. H. Kim, and C. F. Yao, J. Am. Chem. Soc., 1993, 115, 10596.
105. K. Yoshida, J. Chem. Soc., Chem. Comm., 1978, 1108.
106. (a) M. D'Auria, A. De Mico, F. D'Onofrio, and G. Piancatelli, J. Chem. Soc., Perkin Trans. 1, 1987, 1777.
107. (b) M. D'Auria, R. Antonioletti, A. De Mico, and G. Piancatelli, Heterocycles, 1986, 24, 1575.
108. (c) R. Antonioletti, M. D'Auria, A. De Mico, G. Piancatelli, and A. Scettri, J. Chem. Soc., Perkin Trans. 1, 1985, 1285.
109. (d) R. Antonioletti, M. D'Auria, F. D'Onofrio, G. Piancatelli, and A. Scettri, J. Chem. Soc., Perkin Trans. 1, 1986, 1755.
110. (e) R. Antonioletti, M. D'Auria, A. De Mico, G. Piancatelli, and A. Scettri, Tetrahedron, 1985, 41, 3441.
111. M. D'Auria, A. De Mico, F. D'Onofrio, and G. Piancatelli, J. Org. Chem., 1987, 52, 5243.
112. B. Taljaard and G. J. Burger, Adv. Synth. Catal., 2002, 344, 1111.
113. M. D'Auria, G. Piancatelli, and T. Ferri, J. Org. Chem., 1990, 55, 4019.
114. (a) S. Ito, I. Saito, and T. Matsuura, J. Am. Chem. Soc., 1980, 102, 7535.
115. (b) T. Matsuura, I. Saito, S. Ito, H. Sugiyama, and T. Shinmura, Pure Appl. Chem., 1980, 52, 2705.
116. (c) I. Saito, S. Ito, and T. Matsuura, J. Am. Chem. Soc., 1978, 100, 2901.
117. S. Ito, I. Saito, and T. Matsuura, Tetrahedron Lett., 1979, 4067.
118. S. Ito, I. Saito, and T. Matsuura, Tetrahedron 1981, 37, 45.
119. K. Maruyama, T. Otsuki, and S. Tai, J. Org. Chem., 1985, 50, 52.
120. Y. Blache, M.-E. Sinibaldi-Troin, M. Hichour, V. Benezech, O. Chavignon, J.-C. Gramain, J.-C. Teulade, and J.-P. Chapat, Tetrahedron, 1999, 55, 1959.
121. (a) J. Nasielski, A. Kirsch-Demesmacker, P. Kirsch, and R. Nasielski-Hinken, Chem. Comm., 1970, 302.
122. (b) J. Nasielski, A. Kirsch-Demesmacker, and R. Nasielski-Hinken, Tetrahedron, 1972, 28, 3767.
123. (c) J. Nasielski, and A. Kirsch-Demesmacker, Tetrahedron, 1973, 29, 3153.
124. L. R. Hamilton and P. J. Kropp, Tetrahedron Lett., 1971, 1625.
125. (a) A. Profumo, E. Fasani, and A. Albini, Heterocycles, 1999, 51, 1499.
126. (b) E, Fasani, F. F. Barberis Negra, M. Mella, S. Monti, and A. Albini, J. Org. Chem., 1999, 64, 5388.
127. (a) R. Bernardi, T. Caronna, S. Morocchi, M. Ursini, and B. M. Vittimberga, J. Chem. Soc., Perkin Trans. 1, 1990, 97.
128. (b) R. Bernardi, T. Caronna, S. Morocchi, and B. M. Vittimberga J. Chem. Soc., Perkin Trans. 2, 1991, 1411.
129. (c) R. Bernardi, T. Caronna, G. Poggi, and B. M. Vittimberga, J. Heterocycl. Chem., 1994, 31, 903.
130. (d) T. Caronna, B. M. Vittimberga, M. E. Kornn, and W. G. McGimpsey, J. Photochem. Photobiol., A, 1995, 90, 137.
131. K. Mizuno, G. Konishi, T. Nishiyama, and H. Inoue, Chem. Lett., 1995, 1077.
132. M. Igarashi and M. Tada, Heterocycles, 1994, 38, 2277.
133. (a) M. Tada, H. Hamazaki, and H. Hirano, Bull. Chem. Soc. Jpn., 1982, 55, 3865.
134. (b) M. Tada and K. Tsuzuki, Chem. Lett., 1984, 415.
135. K. Mizuno, K. Marukami, N. Kamiyama, and Y. Otsuji, J. Chem. Soc., Chem. Comm., 1983, 462.
136. N. Manoj and K. R. Gopidas, J. Photochem. Photobiol., A, 1995, 85, 53.
137. C. P. Butts, L. Eberson, M. P. Hartshorn, F. Radner, W. T. Robinson, and B. R. Wood, Acta Chem. Scand., 1997, 51, 839.
138. K. Song, M.-L. Peng, M. Xu, L.-Z. Wu, L.-P. Zhang, and C.-H. Tung, Tetrahedron Lett., 2002, 43, 6633.
139. S. Buscemi, A. Pace, N. Vivona, T. Caronna, and A. Galia, J. Org. Chem., 1999, 64, 7028.
140. D. Burdi and T. P. Begley, J. Am. Chem. Soc., 1991, 113, 7768.
141. R. A. Abramovitch, J. M. Beckert, H. H. Gibson Jr., A. Belcher, G. Hundt, T. Sierra, S. Olivella, W. T. Pennigton, and A. Solè, J. Org. Chem., 2001, 66, 1242.
142. D. Doepp, W. A. F. Youssef, A. Dittmann, A. M. Kaddah, A. A. Shalaby, and Y. M. Naguib, J. Inf. Recording, 2000, 25, 57.
143. J. Santamaria, Pure Appl. Chem., 1995, 67, 141.
144. G. Cocquet, P. Rool, and C. Ferroud, Tetrahedron Lett.,2001, 42, 839.
145. J. Santamaria, M. T. Kaddachi, and C. Ferroud, Tetrahedron Lett., 1992, 33, 781.
146. (a) K. Mizuno, S. Toda, and Y. Otsuji, Chem. Lett., 1987, 203.
147. (b) J. Claret, I. Fernandez, C. Galvez, and R. Lapouyade, J. Photochem. Photobiol., A, 1991, 55, 347.
148. M. P. Crozet, J. M. Surzur, P. Vanelle, C. Ghiglione,and J. Maldonado, Tetrahedron Lett., 1985, 26, 1023.
149. (a) C. D. Beadle and W. R. Bowman, J. Chem. Res. (S), 1985, 150.
150. (b) M. P. Crozet, J. M. Surzur, P. Vanelle, C. Ghiglione, and J. Maldonado, Tetrahedron Lett., 1985, 26, 1023.