Reversible formation of iodosylbenzene-iron porphyrin intermediates in the reaction of oxoiron(IV) porphyrin π-cation radicals and iodobenzene

Angewandte Chemie - International Edition

Volumn 42, Issue 1, 2003, Pages 109-111

  Nam, Wonwoo ^a   Choi, Sun Kyung ^a   Lim, Mi Hee ^a   Rohde, Jan Uwe ^b   Kim, Inwoo ^a   Kim, Jinheung ^c   Kim, Cheal ^d   Que Jr , Lawrence ^b  

^a Ewha Womans University   (South Korea)

^b University of Minnesota   (United States)

^c Changwon National University   (South Korea)

^d Seoul National University of Science and Technology   (South Korea)

Author keywords

Enzyme models; Epoxidation; Iron; Porphyrinoids; Radical ions

Indexed keywords

RADICALS;

AROMATIC HYDROCARBONS; IRON; OLEFINS; PORPHYRINS;

COMPLEXATION;

ALKENE; CATION; EPOXIDE; IODOBENZENE; IODOSOBENZENE; IRON COMPLEX; PORPHYRIN DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; EPOXIDATION; MOLECULAR MODEL; REACTION ANALYSIS;

ALKENES; CYCLOHEXENES; EPOXY COMPOUNDS; IODOBENZENES; IRON; METALLOPORPHYRINS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PORPHYRINS; SPECTROPHOTOMETRY; SPECTROPHOTOMETRY, ULTRAVIOLET; STILBENES;

EID: 0037414926     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390036     Document Type: Article

References (38)

1. a) P. R. Ortiz de Montellano, Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed., Plenum, New York, 1995;
2. b) M. Sono, M. P. Roach, E. D. Coulter, J. H. Dawson, Chem. Rev. 1996, 96, 2841-2887;
3. c) J. L. McLain, J. Lee, J. T. Groves in Biomimetic Oxidations Catalyzed by Transition Metal Complexes (Ed.: B. Meunier), Imperial College Press, London, 2000, pp. 91-169;
4. d) B. Meunier, A. Robert, G. Pratviel, J. Bernadou in The Porphyrin Handbook, Vol. 4 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York. 2000, chap. 31, pp. 119-187.
5. a) R. Davydov, T. M. Makris, V. Kofman, D. E. Werst, S. G. Sligar, B. M. Hoffman, J. Am. Chem. Soc. 2001, 123, 1403-1415;
6. b) I. Schlichting, J. Berendzen, K. Chu, A. M. Stock. S. A. Maves, D. A. Benson, R. M. Sweet, D. Ringe, G. A. Petsko, S. G. Sligar, Science 2000, 287, 1615-1622;
7. c) F. Ogliaro, S. Cohen, M. Filatov, N. Harris, S. Shaik, Angew. Chem. 2000, 112, 4009-4013; Angew. Chem. Int. Ed. 2000, 39, 3851-3855.
8. c) F. Ogliaro, S. Cohen, M. Filatov, N. Harris, S. Shaik, Angew. Chem. 2000, 112, 4009-4013; Angew. Chem. Int. Ed. 2000, 39, 3851-3855.
9. a) Y. Watanabe in The Porphyrin Handbook, Vol. 4 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2000, chap. 30, pp. 97-117;
10. b) W. Nam, H. J. Han, S.-Y. Oh, Y. J. Lee, M.-H. Choi, S.-Y. Han, C. Kim, S. K. Woo, W. Shin, J. Am. Chem. Soc. 2000, 122, 8677-8684, and references therein.
11. a) N. Jin, J. L. Bourassa, S. C. Tizio, J. T. Groves. Angew. Chem. 2000, 112, 4007-4009; Angew. Chem. Int. Ed. 2000, 39, 3849-3851;
12. a) N. Jin, J. L. Bourassa, S. C. Tizio, J. T. Groves. Angew. Chem. 2000, 112, 4007-4009; Angew. Chem. Int. Ed. 2000, 39, 3849-3851;
13. b) H.-A. Wagenknecht, W.-D. Woggon, Angew. Chem. 1997, 109, 404-407; Angew. Chem. Int. Ed. Engl. 1997, 36, 390-392.
14. b) H.-A. Wagenknecht, W.-D. Woggon, Angew. Chem. 1997, 109, 404-407; Angew. Chem. Int. Ed. Engl. 1997, 36, 390-392.
15. Abbreviations of porphyrin ligands: TMP=meso-tetramesitylporphinato dianion; TDCPP=meso-tetrakis(2,6-dichlorophenyl)porphinato dianion: TDFPP=meso-tetrakis(2,6-difluorophenyl)porphinato dianion.
16. W. Nam, M. H. Lim, S.-Y. Oh, Inorg. Chem. 2000, 39, 5572-5575.
17. a) J. P. Collman, A. S. Chien, T. A. Eberspacher, J. I. Brauman, J. Am. Chem. Soc. 2000, 122, 11098-11100;
18. b) K. Machii, Y. Watanabe, I. Morishima, J. Am. Chem. Soc. 1995, 117, 6691-6697.
19. K. Jayaraj, J. Terner, A. Gold, D. A. Roberts, R. N. Austin, D. Mandon, R. Weiss, E. Bill, M. Muther, A. X. Trautwein, Inorg. Chem. 1996, 35, 1632-1640.
20. H. Fujii, Coord. Chem. Rev. 2002, 226, 51-60.
21. a) A. L. Roe. D. J. Schneider, R. J. Mayer, J. W. Pyrz, J. Widom, L. Que, Jr., J. Am. Chem. Soc. 1984. 106, 1676-1681;
22. b) C. R. Randall, L. Shu, Y.-M. Chiou, K. S. Hagen, M. Ito, N. Kitajima, R. J. Lachicotte, Y. Zang, L. Que, Jr., Inorg. Chem. 1995, 34, 1036-1039;
23. c) T. E. Westre, P. Kennepohl, J. G. DeWitt, B. Hedman, K. O. Hodgson, E. I. Solomon, J. Am. Chem. Soc. 1997, 119, 6297-6314.
24. a) J. E. Penner-Hahn, T. J. McMurry, M. Renner, L. Latos-Grazynsky, K. S. Eble, I. M. Davis, A. L. Balch, J. T. Groves, J. H. Dawson, K. O. Hodgson, J. Biol. Chem. 1983, 258, 12761-12764;
25. b) T. Wolter, W. Meyer-Klaucke, M. Müther, D. Mandon, H. Winkler, A. X. Trautwein, R. Weiss, J. Inorg. Biochem. 2000, 78, 117-122.
26. B. Meunier, J. Bernadou, in Struct. Bonding (Ed. B. Meunier) Springer, Berlin 2000, 97, 1-35, and references therein.
27. W. Nam, J. S. Valentine, J. Am. Chem. Soc. 1993, 115, 1772-1778.
28. IV-porphyrins oxygenated hydrocarbons and exchanged oxygen atoms with labeled water. a) J. A. Smegal, C. L. Hill, J. Am. Chem. Soc. 1983, 105, 2920-2922; b) J. A. Smegal, B. C. Schardt, C. L. Hill, J. Am. Chem. Soc, 1983, 105, 3510-3515; c) J. A. Smegal, C. L. Hill, J. Am. Chem. Soc. 1983, 105, 3515-3521.
29. IV-porphyrins oxygenated hydrocarbons and exchanged oxygen atoms with labeled water. a) J. A. Smegal, C. L. Hill, J. Am. Chem. Soc. 1983, 105, 2920-2922; b) J. A. Smegal, B. C. Schardt, C. L. Hill, J. Am. Chem. Soc, 1983, 105, 3510-3515; c) J. A. Smegal, C. L. Hill, J. Am. Chem. Soc. 1983, 105, 3515-3521.
30. IV-porphyrins oxygenated hydrocarbons and exchanged oxygen atoms with labeled water. a) J. A. Smegal, C. L. Hill, J. Am. Chem. Soc. 1983, 105, 2920-2922; b) J. A. Smegal, B. C. Schardt, C. L. Hill, J. Am. Chem. Soc, 1983, 105, 3510-3515; c) J. A. Smegal, C. L. Hill, J. Am. Chem. Soc. 1983, 105, 3515-3521.
31. J. S. Valentine, W. Nam, R. Y. N. Ho in The Activation of Dioxygen and Homogeneous Catalytic Oxidation (Eds.: D. H. R. Barton, A. E. Martell, D. T. Sawyer), Plenum, New York, 1993, pp. 183-198, and references therein.
32. -), oxoiron(IV) porphyrin π-cation radicals are the reactive epoxidizing intermediate in the catalytic epoxidation of olefins by PhIO: W. Nam, S. W. Jin, M. H. Lim, J. Y. Ryu, C. Kim, Inorg. Chem. 2002, 41, 3647-3652.
33. The existence of a "second oxidant" in catalytic oxygenation reactions has been a topic of much debate. See the following recent review articles. a) P. R. Ortiz de Montellano, J. J. De Voss, Nat. Prod. Rep. 2002, 19, 477-493; b) Y. Watanabe, J. Biol. Inorg. Chem. 2001, 6, 846-856; c) T. D. H. Bugg, Curr. Opin. Chem. Biol. 2001, 5, 550-555; d) A. D. N. Vaz, Curr. Drug Metab. 2001, 2, 1-16; M. Newcomb, P. H. Toy, Acc. Chem. Res. 2000, 33, 449-455.
34. The existence of a "second oxidant" in catalytic oxygenation reactions has been a topic of much debate. See the following recent review articles. a) P. R. Ortiz de Montellano, J. J. De Voss, Nat. Prod. Rep. 2002, 19, 477-493; b) Y. Watanabe, J. Biol. Inorg. Chem. 2001, 6, 846-856; c) T. D. H. Bugg, Curr. Opin. Chem. Biol. 2001, 5, 550-555; d) A. D. N. Vaz, Curr. Drug Metab. 2001, 2, 1-16; M. Newcomb, P. H. Toy, Acc. Chem. Res. 2000, 33, 449-455.
35. The existence of a "second oxidant" in catalytic oxygenation reactions has been a topic of much debate. See the following recent review articles. a) P. R. Ortiz de Montellano, J. J. De Voss, Nat. Prod. Rep. 2002, 19, 477-493; b) Y. Watanabe, J. Biol. Inorg. Chem. 2001, 6, 846-856; c) T. D. H. Bugg, Curr. Opin. Chem. Biol. 2001, 5, 550-555; d) A. D. N. Vaz, Curr. Drug Metab. 2001, 2, 1-16; M. Newcomb, P. H. Toy, Acc. Chem. Res. 2000, 33, 449-455.
36. The existence of a "second oxidant" in catalytic oxygenation reactions has been a topic of much debate. See the following recent review articles. a) P. R. Ortiz de Montellano, J. J. De Voss, Nat. Prod. Rep. 2002, 19, 477-493; b) Y. Watanabe, J. Biol. Inorg. Chem. 2001, 6, 846-856; c) T. D. H. Bugg, Curr. Opin. Chem. Biol. 2001, 5, 550-555; d) A. D. N. Vaz, Curr. Drug Metab. 2001, 2, 1-16; M. Newcomb, P. H. Toy, Acc. Chem. Res. 2000, 33, 449-455.
37. The existence of a "second oxidant" in catalytic oxygenation reactions has been a topic of much debate. See the following recent review articles. a) P. R. Ortiz de Montellano, J. J. De Voss, Nat. Prod. Rep. 2002, 19, 477-493; b) Y. Watanabe, J. Biol. Inorg. Chem. 2001, 6, 846-856; c) T. D. H. Bugg, Curr. Opin. Chem. Biol. 2001, 5, 550-555; d) A. D. N. Vaz, Curr. Drug Metab. 2001, 2, 1-16; M. Newcomb, P. H. Toy, Acc. Chem. Res. 2000, 33, 449-455.
38. F. Ogliaro, S. P. de Visser, S. Cohen, P. K. Sharma, S. Shaik, J. Am. Chem. Soc. 2002, 124, 2806-2817.