Polyhaloporphyrins: Unusual Ligands for Metals and Metal-Catalyzed Oxidations

Accounts of Chemical Research

Volumn 30, Issue 6, 1997, Pages 251-259

  Dolphin, David ^a,d,e,f   Traylor, Teddy G ^b,c   Xie, Lily Y ^a,d,g,h  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d UCSD ^*

^e UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^f QLT Phototherapeutics   (Canada)

^g PEKING UNIVERSITY   (China)

^h UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000794919     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar960126u     Document Type: Article

References (66)

1. The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978/ 79; Vols. 1-7.
2. Battersby, A. R. Science 1994, 264, 1551-1557.
3. This paper as originally submitted to the Editor cited more than 100 references, which occupied fully one-third of the paper. In order to meet the space criteria of Accounts, we have chosen, where possible, to cite only recent references. A recent monograph gives an excellent up-to-date review of many areas touched upon here. Cytochrome P-450: Structure, Mechanism and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1995.
4. Even the trivial names of porphyrins are frequently complex. In this review the major porphyrins are abbreviated as follows: TPP = mesotetraphenylporphyrin (2a) etc. as shown for structures 2-14.
5. Lindsey, J. S.; Schreimann, I. C.; Hsu, H. C.; Keanney, D. C.; Marguerettuz, A. M. J. Am. Chem. Soc. 1987, 52, 827-836.
6. Groves, J. T.; Nemo, T. E.; Myers, R. S. J. Am. Chem. Soc. 1979, 101, 1032-1033.
7. Groves, J. T.; Haushalter, R. C.; Nakamura, M.; Nemo, T. E.; Evans, B. J. J. Am. Chem. Soc. 1981, 103, 2884-2886.
8. Chang, C. K.; Ebina, F. J. Chem. Soc., Chem. Commun. 1981, 778-779.
9. Traylor, P. S., Dolphin, D.; Traylor, T. G. J. Chem. Soc., Chem. Commun. 1984, 279-280.
10. (a) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314-320.
11. (b) He, G.-X.; Arasasingham, R. D.; Zhang, G.-H.; Bruice, T. C. J. Am. Chem. Soc. 1991, 113, 9828-9833.
12. (a) Grenstaff, M. W.; Hill, M. G.; Birnbaum, E. R.; Schaefer, W. P.; Labinger, J. A.; Gray, H. B. Inorg. Chem., in press.
13. (b) Birnbaum, E. R.; Hodge, J. A.; Grinstaff, M. W.; Schaeffer, W. P.; Henling, L.; Labringer, J. A.; Bercaw, J. E.; Gray, H. B. Inorg. Chem. 1995, 34, 3625-3632.
14. (c) Birnbaum, E. R.; Hodge, J. A.; Grinstaff, M. W.; Schaefer, W. P.; Henling, L.; Labinger, J. A.; Bercaw, J. E.; Gray, H. B. Inorg. Chem. 1995, 34, 3625-3632.
15. (a) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790-5792.
16. (b) Groves, J. T.; Stern, M. K. J. Am. Chem. Soc. 1988, 110, 8628-8638.
17. (a) Ellis, P. E., Jr.; Lyons, J. E. Coord. Chem. Rev. 1990, 105, 181-193.
18. (b) Chen, H. L.; Ellis, P. E., Jr.; Wijesekera, T.; Hagan, TE.; Groh, S. E.; Lyons, J. E.; Ridge, D. P. J. Am. Chem. Soc. 1994, 116, 1086-1089.
19. (c) Lyons, J. E.; Ellis, P. E., Jr.; Myer, H. K., Jr.; Wagner, R. W. J. Catal. 1993, 141, 311-315.
20. (d) Ellis, P. E., Jr.; Lyons, J. E. U.S. Patent Appl. 5,120,882, 1992.
21. (e) Henling, M. L.; Schaeffer, W. P.; Hodge, J. A.; Hughes, M. E.; Gray, H. B.; Lyons, J. E.; Ellis, P. E., Jr. Acta Crystallogr. 1993, C49, 1743-1747.
22. (a) Mansuy, D.; Battioni, P. In Metalloporphyrins in Catalytic Oxidations; Sheldon, R. A., Ed.; Marcel Dekker: New York, 1994; pp 99-132.
23. (b) Artaud, I.; Ben-Aziza, K.; Mansuy, D. J. Org. Chem. 1993, 58, 3373-3380.
24. (c) Thellend, A.; Battioni, P.; Mansuy, D. J. Chem. Soc., Chem. Commun. 1994, 1035-1036.
25. (d) Mansuy, D. Coord. Chem. Rev. 1993, 125, 129-14178.
26. (e) Battioni, P.; Renaud, J. P.; Bartoli, J. F.; Reina-Artiles, M.; Fort, M.; Mansuy, D. J. Am. Chem. Soc. 1988, 110, 8462-8470.
27. (f) Brigaud, O.; Battioni, P.; Mansuy, D.; Giessner-Prettre, C. New J. Chem. 1992, 16, 1031-1038.
28. (a) Pitié, M.; Bernadou, J.; Meunier, B. J. Am. Chem. Soc. 1995, 117, 2935-2936.
29. (b) Gaggero, N.; Robert, A.; Bennadou, J.; Meunier, B. Bull. Soc. Chim. Fr. 1994, 131, 706-712.
30. (c) Sorokon, A.; Robert, A.; Meunier, B. J. Am. Chem. Soc. 1993, 115, 7293-7299.
31. (d) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
32. (e) Hoffman, P.; Meunier, B. New J. Chem. 1992, 16, 559-561.
33. (a) Traylor, T. G.; Kim, C.; Richards, J. L.; Perrin, C. L. J. Am. Chem. Soc. 1995, 117, 3468-3474.
34. (b) Traylor, T. G.; Tsuchiya, S.; Byun, Y.-S.; Kim, C. J. Am. Chem. Soc. 1993, 115, 2775-2781.
35. (c) Traylor, T. G. Pure Appl. Chem. 1991, 63, 265-274.
36. (d) Traylor, T. G.; Hill, K. W.; Fann, W.-P.; Tsuchiya, S.; Bunlap, B. E. J. Am. Chem. Soc. 1992, 114, 1308-1312.
37. Mashiko, T.; Dolphin, D.; Nakano, T.; Traylor, T. G. J. Am. Chem. Soc. 1985, 107, 3735-3736.
38. (18) Dolphin, D.; Forman, A.; Borg, D. C.; Fajer, J.; Felton, R. H. Proc. Natl. Acad. Sci. U.S.A. 1991, 68, 614-618. Dolphin, D.; Felton, R. H. Acc. Chem. Res. 1974, 7, 26-32.
39. Dolphin, D.; Forman, A.; Borg, D. C.; Fajer, J.; Felton, R. H. Proc. Natl. Acad. Sci. U.S.A. 1991, 68, 614-618. Dolphin, D.; Felton, R. H. Acc. Chem. Res. 1974, 7, 26-32.
40. Petsko, G. Personal communication, October 1996.
41. (a) Ohtake, H.; Higuchi, T.; Hirobe, M. J. Am. Chem. Soc. 1992, 114, 10660-10662.
42. (b) Collman, J. P.; Tanaka, H.; Hembre, R. T.; Brauman, J. I. J. Am. Chem. Soc. 1990, 112, 3689-3690.
43. (c) Quid, S.; Ricci, M. Tetrahedron Lett. 1990, 31, 1779-1782.
44. Collman, J. P.; Tanaka, H.; Hembre, R. T.; Brauman, J. I. J. Am. Chem. Soc. 1990, 112, 3689-3690.
45. Querci, C.; Ricci, M. Tetrahedron Lett. 1990, 31, 1779-1782.
46. McCarthy, M. B.; White, R. E. J. Biol. Chem. 1983, 258, 9153-9156.
47. Banfi, S.; Maiocchi, A.; Moggi, A.; Montanari, F.; Quici, S. J. Chem. Soc., Chem. Commun. 1990, 1794-1796.
48. (a) Dolphin, D.; Nakano, T.; Kirk, T. K.; Wijesekera, T. P.; Farrell, R. L.; Maione, T. E. U.S. Patent 4,892,941.
49. (b) Wijesekera, T.; Matsumoto, A.; Dolphin, D.; Lexa, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 1028-1030.
50. Traylor, T. G.; Tsuchiya, S. Inorg. Chem. 1987, 26, 1338-1339.
51. Tsuchiya, S.; Seno, M. Chem. Lett. 1989, 263-266.
52. (a) Lu, W. Y.; Bartoli, J. F.; Battioni, P.; Mansuy, D. New J. Chem. 1992, 16, 621-628.
53. (b) Tabushi, I. Coord. Chem. Rev. 1988, 86, 1-42.
54. Traylor, T. G. Unpublished results.
55. Labinger, J. A. Catal. Lett. 1994, 26, 95-99.
56. Harvey, P. J.; Schoemaker, H. E.; Bowen, R. M.; Palmer, J. M. FEBS Lett. 1985, 183, 13.
57. Chow, J.; Dolphin, D. Unpublished results.
58. (a) Cui, F. Ph.D. Dissertation. University of British Columbia, Vancouver, British Columbia, Canada, 1990.
59. (b) Cui, F.; Dolphin, D. Bioorg. Med. Chem. 1994, 27, 735-742.
60. (c) Cui, F.; Dolphin, D. Can. J. Chem. 1995, 72, 2153-2157.
61. (d) Cui, F.; Wijesekera, T.; Dolphin. D.; Farrell, R.; Skerker, P. J. Biotechnol. 1993, 30, 15-26.
62. Chorghade, M. S.; Hill, D. R.; Lee, E. C.; Pariza, R. J.; Dolphin, D.; Hino, F.; Zhang, L.-Y. Pure Appl. Chem. 1996, 68, 753-756.
63. DiMagno, S. G.; Williams, R. A.; Therien, M. J. J. Org. Chem. 1994, 59, 6943-6948.
64. Barkigia, K. M.; Renner, M. W.; Furenlid, L. R.; Medforth, C. J.; Smith, K. M.; Fajer, J. J. Am. Chem. Soc. 1993, 115, 3627-3635.
65. Kadish, K. M. Prog. Inorg. Chem. 1986, 34, 435.
66. Ochsenbein, P.; Mandon, D.; Fischer, J.; Weiss, R.; Austin, R.; Jayaraj, K.; Gold, A.; Terner, J.; Bill, E.; Müther, M.; Trautwein, A. X. Angew. Chem., Int. Ed. Engl. 1993, 32, 1437-1439.