Photocatalytic oxygenation of anthracenes and olefins with dioxygen via selective radical coupling using 9-mesityl-10-methylacridinium ion as an effective electron-transfer photocatalyst

Journal of the American Chemical Society

Volumn 126, Issue 49, 2004, Pages 15999-16006

  Kotani, Hiroaki ^a   Ohkubo, Kei ^a   Fukuzumi, Shunichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; IRRADIATION; LIGHT ABSORPTION; OXIDATION; OXYGENATORS; PHOTOCATALYSIS; REACTION KINETICS;

ABSORPTION BANDS; PHOTOCATALYTIC OXYGENATION; RADICAL COUPLING REACTIONS;

OLEFINS;

ACETONITRILE; ACRIDINE DERIVATIVE; ALKENE DERIVATIVE; ANTHRACENE DERIVATIVE; ANTHRAQUINONE; ETHYLENE DERIVATIVE; HYDROGEN PEROXIDE; KETONE; OXYGEN;

ABSORPTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON; ELECTRON TRANSPORT; LIGHT IRRADIANCE; OXYGEN SATURATION; OXYGENATION; PHOTOCATALYSIS;

EID: 10444219530     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048353b     Document Type: Article

References (86)

1. Amatore, C.; Brown, A. R. J. Am. Chem. Soc. 1996, 118, 1482.
2. Photoinduced Electron Transfer, Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part A-D.
3. (a) Julliard, M.; Chanon, M. Chem. Rev. 1983, 83, 425.
4. (b) Kavarnos, G. J.; Turro, N. J. Chem. Rev. 1986, 86, 401.
5. Whitten, D. G.; Chesta, C.; Ci, X.; Kellett, M. A.; Yam, V. W. W. In Photochemical Processes in Organised Molecular Systems; Honda, K., Ed.; Elsevier: Amsterdam. 1991.
6. (b) Gaillard, E. R.; Whitten, D. G. Acc. Chem. Res. 1996, 29, 292.
7. Pandey, G. Topics in Current Chemistry; Photoinduced Electron-Transfer V; Springer-Verlag; Berlin, 1993; Vol. 168, pp 175-221.
8. (a) Mangion, D.; Arnold, D. R. Acc. Chem. Res. 2002, 35, 297.
9. (b) Miyashi, T.; Ikeda, H.; Takahashi, Y. Acc. Chem. Res. 1999, 32, 815.
10. (a) Yoon, U. C.; Mariano, P. S.; Givens, R. S.; Atwater, B. W. In Advances in Electron-Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 4, pp 117-205.
11. (b) Roth, H. D. In Topics in Current Chemistry: Photoinduced Electron-Transfer IV; Mattay, J., Ed.; Springer-Verlag: Berlin, 1992; Vol. 163, pp 131-245.
12. (c) Saeva, F. D. In Advances in Electron-Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 4, pp 1-25.
13. (a) Fukuzumi, S. In Advances in Electron-Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: Greenwich, CT, 1992; Vol. 2, pp 67-175.
14. (b) Fukuzumi, S.; Itoh, S. In Advances in Photochemistry; Neckers, D. C., Volman, D. H., Eds.; John Wiley & Sons: New York, 1999; Vol. 25. p 107.
15. (c) Sancar, A. In Advances in Electron-Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: Greenwich, CT, 1992; Vol. 2, pp 215-272.
16. (a) Mattes, S. L.; Fand, S. Acc. Chem. Res. 1982, 15, 80.
17. (b) Mattes, S. L.; Farid, S. In Organic Photochemistry; Padwa, A., Ed.; Dekker: New York, 1983; Vol. 6, pp 233-326.
18. (c) Mattay, J.; Vondenhof, M. In Topics in Current Chemistry: Photoinduced Electron-Transfer III; Mattay, J., Ed.; Springer-Verlag: Berlin. 1990; Vol. 159. pp 219-255.
19. (c) Müller, F.; Mattay, J. Chem. Rev. 1993, 93, 99.
20. (a) Schmoldt, P.; Rinderhagen, H.; Mattay, J. Mol. Supramol. Chem. 2003, 9, 185.
21. (b) Ulmer, L.; Siedschlag, C.; Mattay, J. Eur. J. Org. Chem. 2003, 3811.
22. (a) Lewis, F. D. In Photoinduced Electron Transfer: Fox, M. A., Chanon, M., Ed.; Elsevier: Amsterdam, 1988; Part C, pp 1-69.
23. (b) Bauld, N. L. In Advances in Electron-Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: Greenwich; CT, 1992; Vol. 2, pp 1-66.
24. (a) Gotoh, T.; Padias, A. B.; Hall, H. K., Jr. J. Am. Chem. Soc. 1991, 113, 1308
25. (b) Mattay, J.; Trampe, G.; Runsink, J. Chem. Ber. 1988, 121, 1991.
26. (c) Takahashi, Y.; Kochi, J. K. Chem. Ber. 1988, 121, 253.
27. (d) Kim, E.; Christi, M.; Kochi, J. K. Chem. Ber. 1990, 123, 1209.
28. (a) Mikami, K.; Matsumoto, S.; Tonoi, T.; Okubo, Y.; Suenobu, T.; Fukuzumi, S. Tetrahedron Lett. 1998, 39, 3733.
29. (b) Mikami, K.; Matsumoto, S.; Okubo, Y.; Fujitsuka, M.; Ito, O.; Suenobu, T.; Fukuzumi, S. J. Am. Chem. Soc. 2000, 122, 2236.
30. (c) Vassilikogiannakis, G.; Orfanopoulos, M. Tetrahedron Lett. 1997, 38, 4323.
31. (a) Bockman, T. M.; Perrier, S.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 1993, 595.
32. (b) Bockman, T. M.; Shukla, D.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 1996, 1623.
33. (a) Sun, D.; Hubig, S. M.; Kochi, J. K. J. Photochem. Photobiol., A 1999. 122, 87.
34. (b) Sun, D.; Hubig, S. M.; Kochi, J. K. J. Org. Chem. 1999, 64, 2250.
35. Fukuzumi, S.; Okamoto, T.; Ohkubo, K. J. Phys. Chem. A 2003, 107, 5412.
36. (a) Stevens, B. Adv. Photochem. 1971, 8, 161.
37. (b) Saltiel, J.; Townsend, D. E.; Watson, B. D.; Shannon, P.; Pinson, S. L. J. Am. Chem. Soc. 1977. 99, 884.
38. (c) Bergmark, W. R.; Jones, G., II.; Reinhardt, T. E.; Halpern, A. M. J. Am. Chem. Soc. 1978, 100, 6665.
39. (d) Saltiel, J.; Marchand, G. R.; Smothers, W. K.; Stout, S. A.; Charlton, J. L. J. Am. Chem. Soc. 1981, 103, 7159.
40. (e) Charlton, J. L.; Dabestani, R.; Saltiel, J. J. Am. Chem. Soc. 1983, 105, 3473.
41. Manring, L. E.; Peters, K. S.; Jones, G., II.; Bergmark, W. R. J. Am. Chem. Soc. 1985, 107, 1485.
42. Schaefer, C.; Mattay, J. Photochem. Pholobiol. Sci. 2004, 3, 331.
43. (a) Gust, D.; Moore, T. A.; Moore, A. L. In Electron Transfer in Chemistry, Balzani, V. Ed: Wiley-VCH: Weinheim. 2001; Vol. 3. pp 272-336.
44. (b) Gust, D.; Moore, T. A. In The Porphyrin Handbook: Radish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA. 2000; Vol. 8, pp 153-190.
45. (c) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40.
46. (a) Wasielewski, M. R. Chem. Rev. 1992, 92, 435.
47. (b) Debreczeny, M. P.; Svec, W. A.; Wasielewski, M. R. Science 1996, 274, 584.
48. (c) Osuka, A.; Mataga, N.; Okada, T. Pure Appl. Chem. 1997, 69, 797.
49. (a) Jordan, K. D.; Paddon-Row, M. N. Chem. Rev. 1992, 92, 395.
50. (b) Paddon-Row: M. N. Acc. Chem. Res. 1994, 27, 18.
51. (c) Verhoeven, J. W. Adv. Chem. Phys. 1999, 106, 603.
52. (d) Paddon-Row, M. N. Adv. Phys. Orig. Chem. 2003, 38, 1.
53. (a) Harriman, A.; Sauvage, J.-P. Chem. Soc. Rev. 1996, 25, 41.
54. (b) Blanco, M.-J.; Consuelo Jiménez, M.; Chambron, J.-C.; Heitz, V.; Linke, M.; Sauvage, J.-P. Chem. Soc. Rev. 1999, 28, 293.
55. (c) Chambron, J.-C.; Collin. J.-P.; Dalbavie, J.-O.; Dietrich-Buchecker, C. O.; Heitz, V.; Odobel, F.; Solladié, N.; Sauvage, J.-P. Coord. Chem. Rev. 1998, 178-180, 1299.
56. Fukuzumi, S.; Guldi, D. M. In Electron Transfer in Chemistry, Balzani. V. Ed.; Wiley-VCH: Weinheim, 2001; Vol. 2. pp 270-337.
57. (b) Fukuzumi, S. Org. Biomol. Chem. 2003, 1, 609.
58. Fukuzumi, S.; Kotani, H.; Ohkubo, K.; Ogo, S.; Tkachenko, N. V.; Lemmetyinen, H. J. Am. Chem. Soc. 2004, 126, 1600.
59. Active Oxygen in Chemistry. Foote, C. S., Valentine, J. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional: New York. 1995; Vol. 2.
60. Denkers, R. L.; Workentin, M. S. J. Am. Chem. Soc. 2004, 126, 1688.
61. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, 4th ed.; Pergamon Press: Elmsford, NY, 1996.
62. Foote, C. S.; Wexler, S.; Ando, W.; Higgins, R. J. Am. Chem. Soc. 1968, 90, 975.
63. Mair, R. D.; Graupner, A. J. Anal. Chem. 1964, 36, 194.
64. (a) Fukuzumi, S.; Kuroda, S.; Tanaka, T. J. Am. Chem. Soc. 1985, 107, 3020.
65. (b) Fukuzumi, S.; Ishikawa, M.; Tanaka, T. J. Chem. Soc., Perkin Trans. 2 1989, 1037.
66. Hatchard, C. G.; Parker, C. A. Proc. R. Soc. London. Ser. A 1956, 255, 518.
67. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
68. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
69. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory: Wiley: New York, 1986.
70. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian, Inc.; Pittsburgh PA, 1998.
71. Luo, C.; Fujitsuka, M.; Watanabe, A.; Ito, O.; Gan, L.; Huans, Y.; Huang, C.-H. J. Chem. Soc., Faraday Trans. 1998, 94, 527.
72. Ohkubo, K.; Kotani, H.; Shao, J.; Ou, Z.; Kadish, K. M.; Li, G.; Pandey, R. K.; Fujitsuka, M.; Ito, O.; Imahori, H.; Fukuzumi, S. Angew. Chem., Int. Ed. 2004, 43, 853.
73. Fukuzumi, S.; Nakanishi, I.; Tanaka, K. J. Phys. Chem. A 1999, 103, 11212.
74. Fukuzumi, S.; Ohkubo, K.; Okamoto, T. J. Am. Chem. Soc. 2002, 124. 14147.
75. Lind, J.; Shen, X.; Merényi, G.; Jonsson, B. Ö. J. Am. Chem. Soc. 1989, 111, 7654.
76. (a) Bagchi, R. N.; Bond, A. M.; Scholz, F.; Stösser, R. J. Am. Chem. Soc. 1989, 111, 8270.
77. (b) Ohkubo, K.; Menon, S. C.; Orita, A.; Otera, J.; Fukuzumi, S. J. Org. Chem. 2003, 68, 4720.
78. (a) Araki, Y.; Dobrowolski, D. C.; Goyne, T. E.; Hanson, D. C.; Jians, Z. Q.; Lee, K. J.; Foote, C. S. J. Am. Chem. Soc. 1984, 106, 4570.
79. (b) Fukuzumi, S.; Fujita, S.; Suenobu, T.; Yamada, H.; Imahori, H.; Araki, Y.; Ito, O. J. Phys. Chem. A 2002, 106, 1241.
80. Eriksen, J.; Foote, C. S.; Parker, T. L. J. Am. Chem. Soc. 1977, 99, 6455.
81. Kabe, Y.; Takata, T.; Ueno, K.; Ando, W. J. Am. Chem. Soc. 1984, 106, 8174.
82. Akaba, R.; Sakuragi, H.; Tokumaru, K. J. Chem. Soc., Perkin Trans. 2 1991, 291.
83. da Hora Mashado, A. E.; de Andrade, M. L.; Severino, D. J. Photochem. Photobiol., A 1995, 91, 179.
84. Fox M. A. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 1, pp 271-311.
85. Fox, M. A.; Chen, C.-C. J. Am. Chem. Soc. 1981, 103, 6757.
86. 2 (Scheme 2). However, the detailed mechanism has yet to be clarified.