Photocatalytic electron-transfer oxidation of triphenylphosphine and benzylamine with molecular oxygen via formation of radical cations and superoxide ion

Bulletin of the Chemical Society of Japan

Volumn 79, Issue 10, 2006, Pages 1489-1500

  Ohkubo, Kei ^a   Nanjo, Takashi ^a   Fukuzumi, Shunichi ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; OXIDATION; OXYGEN; PARAMAGNETIC RESONANCE; PHOTOCHEMICAL REACTIONS; POSITIVE IONS; REACTION KINETICS;

BENZYLAMINE; PHOTOIRRADIATION; SUPEROXIDES; TRIPHENYLPHOSPHINE;

AROMATIC COMPOUNDS;

9 MESITYL 10 METHYLACRIDINIUM PERCHLORIC ACID; BENZYLAMINE; CATION; HYDROGEN PEROXIDE; OXYGEN; PERCHLORIC ACID; SUPEROXIDE; TRIPHENYLPHOSPHINE; TRIPHENYLPHOSPHINE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; OXIDATION; PHOTOCATALYSIS; PHOTOLYSIS; PHOTOOXIDATION;

EID: 33750600196     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.79.1489     Document Type: Article

References (103)

1. J. Fossey, D. Lefort, J. Sorba, Free Radicals in Organic Chemistry, Wiley, New York, 1995.
2. B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, ed. by J. E. Baldwin, Pergamon Press, Oxford, 1986.
3. a) Radicals in Organic Synthesis, ed. by P. Renaoud, M. P. Sibi, Wiley-VCH, Weinheim, 2001, Vol. 2.
4. b) H. Togo, Advanced Free Radical Reactions for Organic Synthesis, Elsevier, Amsterdam, 2004.
5. Free Radicals in Biology and Environment, ed. by F. Minisci, Kluwer, Dordrecht, 1997.
6. M. Schmittel, M. K. Ghorai, Electron Transfer in Chemistry, ed. by V. Balzani, Wiley-VCH, Weinheim, 2001, Vol. 2, pp. 5-54.
7. L. Eberson, Electron Transfer Reactions in Organic Chemistry: Reactivity and Structure, Springer, Heidelberg, 1987, Vol. 25.
8. S. Fukuzumi, Advances in Electron Transfer Chemistry, ed. by P. S. Mariano, JAI Press, Greenwich, 1992, Vol. 2, p. 65.
9. S. Fukuzumi, Electron Transfer in Chemistry, ed. by V. Balzani, Wiley-VCH, Weinheim, 2001, Vol. 4, pp. 3-67.
10. S. Das, V. Suresh, Electron Transfer in Chemistry, ed. by V. Balzani, Wiley-VCH, Weinheim, 2001, Vol. 2, pp. 379-456.
11. C. Amatore, A. R. Brown, J. Am. Chem. Soc. 1996, 118, 1482.
12. a) S. Fukuzumi, K. Ohkubo, T. Okamoto, J. Am. Chem. Soc. 2002, 124, 14147.
13. b) S. Fukuzumi, Y. Fujii, T. Suenobu, J. Am. Chem. Soc. 2001, 123, 10191.
14. Photoinduced Electron Transfer, ed. by M. A. Fox, M. Chanon, Elsevier, Amsterdam, 1988.
15. a) F. Müller, J. Mattay, Chem. Rev. 1993, 93, 99.
16. b) M. Mella, M. Fagnoni, M. Freccero, E. Fasani, A. Albini, Chem. Soc. Rev. 1998, 27, 81.
17. a) M. Julliard, M. Chanon, Chem. Rev. 1983, 83, 425.
18. b) F. D. Lewis, Acc. Chem. Res. 1986, 19, 401.
19. c) U. C. Yoon, P. S. Mariano, Acc. Chem. Res. 1992, 25, 233.
20. G. J. Kavarnos, N. J. Turro, Chem. Rev. 1986, 86, 401.
21. E. R. Gaillard, D. G. Whitten, Acc. Chem. Res. 1996, 29, 292.
22. S. Fukuzumi, H. Imahori, Photochemistry of Organic Molecules in Isotropic and Anisotropic Media, ed. by V. Ramamurthy, K. S. Schanze, Marcel Dekker, New York, 2003, pp. 227-273.
23. S. M. Hubig, J. K. Kochi, Electron Transfer in Chemistry, ed. by V. Balzani, Wiley-VCH, Weinheim, 2001, Vol. 2, pp. 618-676.
24. a) J. K. Kochi, Angew. Chem., Int. Ed. Engl. 1988, 27, 1227.
25. b) R. Rathore, J. K. Kochi, Adv. Phys. Org. Chem. 2000, 35, 193.
26. S. Fukuzumi, K. Mochida, J. K. Kochi, J. Am. Chem. Soc. 1979, 101, 5961.
27. G. J. Kavarnos, N. J. Turro, Chem. Rev. 1986, 86, 401.
28. D. G. Whitten, C. Chesta, X. Ci, M. A. Kellett, V. W. W. Yam, In Photochemical Processes in Organized Molecular Systems, ed. by K. Honda, Elsevier, Amsterdam, 1991.
29. G. Pandey, In Topics in Current Chemistry: Photoinduced Electron Transfer V, Springer-Verlag, Berlin, 1993, Vol. 168, pp. 175-221.
30. a) D. Mangion, D. R. Arnold, Acc. Chem. Res. 2002, 35, 297.
31. b) T. Miyashi, H. Ikeda, Y. Takahashi, Acc. Chem. Res. 1999, 32, 815.
32. a) U. C. Yoon, P. S. Mariano, R. S. Givens, B. W. Atwater, In Advances in Electron Transfer Chemistry, ed. by P. S. Mariano, P. S. JAI Press, Greenwich, CT, 1994, Vol. 4, pp. 117-205.
33. b) H. D. Roth, In Topics in Current Chemistry: Photoinduced Electron Transfer IV, ed. by J. Mattay, Springer-Verlag, Berlin, 1992, Vol. 163, pp. 131-245.
34. c) F. D. Saeva, In Advances in Electron Transfer Chemistry, ed. by P. S. Mariano, JAI Press, Greenwich, CT, 1994, Vol. 4, pp. 1-25.
35. a) S. Fukuzumi, In Advances in Electron Transfer Chemistry, ed. by P. S. Mariano, JAI Press, Greenwich, CT, 1992, Vol. 2, pp. 67-175.
36. b) S. Fukuzumi, S. Itoh, In Advances in Photochemistry, ed. by D. C. Neckers, D. H. Volman, John Wiley & Sons, New York, 1999, Vol. 25, p. 107.
37. c) A. Sancar, In Advances in Electron Transfer Chemistry, ed. by P. S. Mariano, JAI Press, Greenwich, CT, 1992, Vol. 2, pp. 215-272.
38. J. Lind, X. Shen, G. Merényi, B. Ö. Jonsson, J. Am. Chem. Soc. 1989, 111, 7654.
39. a) M. S. McDowell, J. H. Espenson, A. Bakac, Inorg. Chem. 1984, 23, 2232.
40. b) K. Zahir, J. H. Espenson, A. Bakac, J. Am. Chem. Soc. 1988, 110, 5059.
41. L. Eberson, R. Gonzales-Luque, J. Lorentzon, M. Merchan, B. O. Roos, J. Am. Chem. Soc. 1993, 115, 2898.
42. E. G. German, A. M. Kuznetsov, I. Efremenko, M. Sheintuch, J. Phys. Chem. A 1999, 103, 10699.
43. S. Fukuzumi, S. Fujita, Y. Suenobu, H. Yamada, H. Imahori, Y. Araki, O. Ito, J. Phys. Chem. A 2002, 106, 1241.
44. a) C. S. Foote, Acc. Chem. Res. 1968, 1, 104.
45. b) C. S. Foote, E. L. Clennan, Properties and Reactions of Singlet Oxygen, In Active Oxygen in Chemistry, ed. by C. S. Foote, J. S. Valentine, A. Greenberg, J. F. Liebman, Chapman and Hall, New York, 1995, pp. 105-140.
46. a) D. R. Kearns, Chem. Rev. 1971, 71, 395.
47. b) L. M. Stephenson, M. J. Grdina, M. Orfanopoulos, Acc. Chem. Res. 1980, 13, 419.
48. a) Singlet Oxygen Reactions with Organic Compounds and Polymers, ed. by B. Ranby, J. F. Rabeck, Wiley, New York, 1978.
49. b) Singlet Oxygen, ed. by A. A. Frimer, CRC Press, Boca Raton, FL, 1985, Vols. I-IV.
50. c) A. Griesbeck, In CRC Handbook of Organic Photochemistry and Photobiology, ed. by W. M. Horspool, P.-S. Song, CRC Press, Boca Raton, FL, 1995, p. 301.
51. M. A. Iesce, Synthetic Organic Photochemistry, ed. by A. G. Greisbeck, J. Mattay, Marcel Dekker, New York, 2005, pp. 299-363.
52. S. Fukuzumi, H. Kotani, K. Ohkubo, S. Ogo, N. V. Tkachenko, H. Lemmetyinen, J. Am. Chem. Soc. 2004, 126, 1600.
53. K. Ohkubo, H. Kotani, S. Fukuzumi, Chem. Commun. 2005, 4520.
54. H. Kotani, K. Ohkubo, S. Fukuzumi, J. Am. Chem. Soc. 2004, 126, 15999.
55. K. Ohkubo, T. Nanjo, S. Fukuzumi, Org. Lett. 2005, 7, 4265.
56. 38
57. S. Fukuzumi, S. Koumitsu, K. Hironaka, T. Tanaka, J. Am. Chem. Soc. 1987, 109, 305.
58. K. J. Smith, E. D. Bergbreiter, M. Newcomb, J. Org. Chem. 1985, 50, 4549.
59. R. D. Mair, A. J. Graupner, Anal. Chem. 1964, 36, 194.
60. S. Fukuzumi, S. Kuroda, T. Tanaka, J. Am. Chem. Soc. 1985, 107, 3020.
61. S. Fukuzumi, M. Ishikawa, T. Tanaka, J. Chem. Soc., Perkin Trans. 2 1989, 1037.
62. C. G. Hatchard, C. A. Parker, Proc. R. Soc. London, Ser. A 1956, 235, 518.
63. K. Ohkubo, K. Suga, K. Morikawa, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 12850.
64. A. J. Bard, L. R. Faulkner, Electrochemical Methods: Fundamentals and Applications, John Wiley & Sons, New York, 2001, Chap. 10, pp. 368-416.
65. The SHACV method provides a superior approach to directly evaluating the one-electron redox potentials in the presence of a follow-up chemical and reaction, relative to the better-known dc and fundamental harmonic ac methods. See: a) M. R. Wasielewski, R. Breslow, J. Am. Chem. Soc. 1976, 98, 4222.
66. b) E. M. Arnett, K. Amarnath, N. G. Harvey, J. Cheng, J. Am. Chem. Soc. 1990, 112, 344.
67. C. K. Mann, K. K. Barnes, In Electrochemical Reactions in Non-aqueous Systems, Mercel Dekker, New York, 1970.
68. a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
69. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
70. c) W. J. Hehre, L. Radom, P. V. R. Schleyer, J. A. Pople, In Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
71. 2P(=O)OPh was detected.
72. S. Tsuji, M. Kondo, K. Ishiguro, Y. Sawaki, J. Org. Chem. 1993, 58, 5055.
73. M. Nakamura, M. Miki, T. Majima, J. Chem. Soc., Perkin Trans. 2 2000, 1447.
74. • moiety at the shorter wavelengths.
75. G. J. Kavarnos, Fundamentals of Photoinduced Electron Transfer, Wiley-VCH, New York, 1993.
76. D. G. Ho, R. Gao, J. Celaje, H.-Y. Chung, M. Selke, Science 2003, 302, 259.
77. Z. B. Alfassil, P. Neta, B. Beaver, J. Phys. Chem. A 1997, 101, 2153.
78. S. Yasui, S. Tojo, T. Majima, J. Org. Chem. 2005, 70, 1276.
79. R. Battio, H. L. Clever, C. L. Young, IUPAC Solubility Data Series, Pergamon Press, Oxford, 1981, Vol. 7.
80. 47 See: a) K. Suga, K. Ohkubo, S. Fukuzumi, J. Phys. Chem. A 2003, 107, 4339.
81. b) K. Suga, K. Ohkubo, S. Fukuzumi, J. Phys. Chem. A 2005, 109, 10168.
82. c) K. Suga, K. Ohkubo, S. Fukuzumi, J. Phys. Chem. A 2006, 110, 3860.
83. d) K. Ohkubo, K. Suga, S. Fukuzumi, Chem. Commun. 2006, 2018.
84. +-catalyzed photooxidation since the photocatalyst was decomposed by the formation of a large amount of the adducts.
85. F. D. Lewis, T.-I. Ho, J. Am. Chem. Soc. 1977, 99, 7991.
86. a) C. G. Shaefer, K. S. Peter, J. Am. Chem. Soc. 1980, 102, 7567.
87. b) F. D. Lewis, Acc. Chem. Res. 1986, 19, 401.
88. P. J. Krusic, J. K. Kochi, J. Am. Chem. Soc. 1968, 90, 7155.
89. a) J. K. Kochi, P. J. Krusic, D. R. Eaton, J. Am. Chem. Soc. 1969, 91, 1877.
90. b) P. J. Krusic, J. K. Kochi, J. Am. Chem. Soc. 1969, 91, 3938.
91. c) P. J. Krusic, J. K. Kochi, J. Am. Chem. Soc. 1969, 91, 3942.
92. d) J. K. Kochi, P. J. Krusic, J. Am. Chem. Soc. 1969, 91, 3944.
93. e) J. A. Howard, E. Furimsky, Can. J. Chem. 1974, 52, 555.
94. a) S. Fukuzumi, K. Shimoosako, T. Suenobu, Y. Watanabe, J. Am. Chem. Soc. 2003, 125, 9074.
95. b) H. Kitaguchi, K. Ohkubo, S. Ogo, S. Fukuzumi, J. Am. Chem. Soc. 2005, 127, 6605.
96. c) K. Ohkubo, Y. Moro-oka, S. Fukuzumi, Org. Biomol. Chem. 2006, 4, 999.
97. ESR measurements of the hydrogen-abstracted radical of benzylamine in Figs. 8 and 9 were carried out under same experimental and instrumental conditions i.e., concentration, temperature, and modulation width.
98. a) S. Naya, H. Ohtoshi, M. Nitta, J. Org. Chem. 2006, 71, 176.
99. b) S. Naya, J. Nishimura, M. Nitta, J. Org. Chem. 2005, 70, 9780.
100. F. D. Lewis, T.-I. Ho, J. T. Sinpson, J. Am. Chem. Soc. 1982, 104, 1924.
101. J. E. Wertz, J. R. Bolton, In Electron Spin Resonance, Elementary Theory and Practical Applications, McGraw-Hill, New York, 1972.
102. S. Fukuzumi, T. Okamoto, K. Ohkubo, J. Phys. Chem. A 2003, 107, 5412.
103. T. Da Ros, M. Prato, D. M. Guldi, M. Ruzzi, L. Pasimeni, Chem. Eur. J. 2001, 7, 816.