Oxidations catalyzed by metallocorroles

Advanced Synthesis and Catalysis

Volumn 346, Issue 2-3, 2004, Pages 165-170

  Gross, Zeev ^a,c,d,e,f   Gray, Harry B ^b,g,h,i,j  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^c BAR ILAN UNIVERSITY   (Israel)

^d Physical Organic Chemistry   (Israel)

^e PRINCETON UNIVERSITY   (United States)

^f Department of Chemistry ^*  (Israel)

^g CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^h NORTHWESTERN UNIVERSITY   (United States)

ⁱ UNIVERSITY OF COPENHAGEN   (Denmark)

^j Och Spine at New York Presbyterian Hospitals   (United States)

more..

Author keywords

Catalytic oxidation; Chromium; Dioxygen activation; Manganese; Metallocorroles

Indexed keywords

CHROMIUM DERIVATIVE; IRON DERIVATIVE; MANGANESE DERIVATIVE;

CATALYSIS; CATALYST; CHELATION; OXIDATION KINETICS; REACTION ANALYSIS; REVIEW; SYNTHESIS;

EID: 1942439087     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303145     Document Type: Review

References (46)

1. For the first reports of corroles, see: a) A. W. Johnson, I. T. Kay, Proc. Chem. Soc. London 1964, 89; b) A. W. Johnson, I. T. Kay, J. Chem. Soc. 1965, 1620; c) A. W. Johnson, I. T. Kay, Proc. Royal Soc. London, Ser. A-Math. Phys. Sci. 1965, 288, 334.
2. For the first reports of corroles, see: a) A. W. Johnson, I. T. Kay, Proc. Chem. Soc. London 1964, 89; b) A. W. Johnson, I. T. Kay, J. Chem. Soc. 1965, 1620; c) A. W. Johnson, I. T. Kay, Proc. Royal Soc. London, Ser. A-Math. Phys. Sci. 1965, 288, 334.
3. For the first reports of corroles, see: a) A. W. Johnson, I. T. Kay, Proc. Chem. Soc. London 1964, 89; b) A. W. Johnson, I. T. Kay, J. Chem. Soc. 1965, 1620; c) A. W. Johnson, I. T. Kay, Proc. Royal Soc. London, Ser. A-Math. Phys. Sci. 1965, 288, 334.
4. For a review that covers the synthesis of corroles up to 1999, see: R. Paolesse, in: The Porphyrin Handbook, Vol. 2 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2000, pp. 201-232.
5. For a review that covers the coordination chemistry of corroles up to 1999, see: C. Erlen, S. Will, K. M. Kadish, in: The Porphyrin Handbook, Vol. 2 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2000, pp. 233-300.
6. Z. Gross, L. Simkhovich, N. Galili, Chem. Commun. 1999, 599-600.
7. For the new triarylcorroles introduced during 1999, see: a) Z. Gross, N. Galili, I. Saltsman, Angew. Chem. Int. Ed. 1999, 38, 1427-1429; b) Z. Gross, N. Galili, L. Simkhovich, I. Saltsman, M. Botoshansky, D. Bläser, R. Boese, I. Goldberg, Org. Lett. 1999, 1, 599-602; c) R. Paolesse, L. Jaquinod, D. J. Nurco, S. Mini, F. Sagone, T. Boschi, K. M. Smith, K. M., Chem. Commun. 1999, 1307-1308.
8. For the new triarylcorroles introduced during 1999, see: a) Z. Gross, N. Galili, I. Saltsman, Angew. Chem. Int. Ed. 1999, 38, 1427-1429; b) Z. Gross, N. Galili, L. Simkhovich, I. Saltsman, M. Botoshansky, D. Bläser, R. Boese, I. Goldberg, Org. Lett. 1999, 1, 599-602; c) R. Paolesse, L. Jaquinod, D. J. Nurco, S. Mini, F. Sagone, T. Boschi, K. M. Smith, K. M., Chem. Commun. 1999, 1307-1308.
9. For the new triarylcorroles introduced during 1999, see: a) Z. Gross, N. Galili, I. Saltsman, Angew. Chem. Int. Ed. 1999, 38, 1427-1429; b) Z. Gross, N. Galili, L. Simkhovich, I. Saltsman, M. Botoshansky, D. Bläser, R. Boese, I. Goldberg, Org. Lett. 1999, 1, 599-602; c) R. Paolesse, L. Jaquinod, D. J. Nurco, S. Mini, F. Sagone, T. Boschi, K. M. Smith, K. M., Chem. Commun. 1999, 1307-1308.
10. For a review about the new synthetic methods for triarylcorroles, see: D. T. Gryko, Eur. J. Org. Chem. 2002, 11, 1735-1743.
11. For utilization of corroles as cyclopropanation catalysts, see: a) L. Simkhovich, A. Mahammed, I. Goldberg, Z. Gross, Chem. Eur. J. 2001, 7, 1041-1055; b) L. Simkhovich, I. Goldberg, Z. Gross, J. Porphyrins Phthalocyanines 2002, 6, 439-444.
12. For utilization of corroles as cyclopropanation catalysts, see: a) L. Simkhovich, A. Mahammed, I. Goldberg, Z. Gross, Chem. Eur. J. 2001, 7, 1041-1055; b) L. Simkhovich, I. Goldberg, Z. Gross, J. Porphyrins Phthalocyanines 2002, 6, 439-444.
13. For utilization of corroles as aziridination catalysts, see: L. Simkhovich, Z. Gross, Tetrahedron Lett. 2001, 42, 8089-8092.
14. 2, see: J. Grodkowski, P. Neta, E. Fujita, A. Mahammed, L. Simkhovich, Z. Gross, J. Phys. Chem. A 2002, 106, 4772-4778.
15. For a medicinal application of corroles, see: A. Segev, D. Aviezer, M. Safran, Z. Gross, A. Yayon, Cardiovasc. Res. 2002, 53, 232-241.
16. B. Meunier, in: Metalloporphyrin Catalyzed Oxidations, (Eds.: F. Montanari, L. Casella), Kluwer, Dordrecht, 1994, pp. 1-48.
17. J. T. Groves, W. J. Kruper, J. Am. Chem. Soc. 1979, 101, 7613-7615.
18. J. T. Groves, R. C. Haushalter, M. Nakamura, T. E. Nemo, B. J. Evans. J. Am. Chem. Soc. 1981, 103, 2884-2886.
19. N. Jin, J. T. Groves, J. Am. Chem. Soc. 1999, 121, 2923-2924.
20. a) Y. Matsuda, S. Yamada, Y. Murakami, Inorg. Chim. Acta 1980, 44, L309-311;
21. b) Y. Murakami, Y. Matsuda, S. Yamada, J. Chem. Soc. Dalton Trans. 1981, 855-861.
22. Z. Gross, J. Biol. Inorg. Chem. 2001, 6, 733-738.
23. A. E. Meier-Callahan, H. B. Gray, Z. Gross, Inorg. Chem. 2000, 39, 3605-3607.
24. T. J. Collins, C. Slebodnick, E. S. Uffelman, Inorg. Chem. 1990, 29, 3433-3436.
25. K. Srinivasan, J. K. Kochi, Inorg. Chem. 1985, 24, 4671.
26. A. E. Meier-Callahan, A. J. Di Bilio, L. Simkhovich, A. Mahammed, I. Goldberg, H. B. Gray, Z. Gross, Inorg. Chem. 2001, 40, 6788-6793.
27. A. Mahammed, H. B. Gray, A. E. Meier-Callahan, Z. Gross, J. Am. Chem. Soc. 2003, 125, 1162-1163.
28. Z. Gross, G. Golubkov, L. Simkhovich, Angew. Chem. Int. Ed. 2000, 39, 4045-4047.
29. B. S. Mandimutsira, B. Ramdhanie, R. C. Todd, H. L. Wang, A. A. Zareba, R. S. Czemuszewicz, D. P. Goldberg, J. Am. Chem. Soc. 2002, 124, 15170-15171.
30. J. P. Collman, L. Zeng, R. A. Decréau, Chem. Commun. 2003, 2974-2975.
31. S. P. de Visser, F. Ogliaro, Z. Gross, S. Shaik, Chem. Eur. J. 2001, 7, 4954-4960.
32. T. Strassner, K. N. Houk, Org. Lett. 1999, 1, 419.
33. G. Golubkov, J. Bendix, H. B. Gray, A. Mahammed, I. Goldberg, A. J. DiBilio, Z. Gross, Angew. Chem. Int. Ed. 2001, 40, 2132-2134.
34. S. P. de Visser, F. Ogliaro, N. Harris, S. Shaik, J. Am. Chem. Soc. 2001, 123, 3037-3047.
35. H. Y. Liu, T. S. Lai, L. L. Yeung, C. K. Chang, Org. Lett. 2003, 5, 617-620.
36. J. Bendix, G. Golubkov, H. B. Gray, Z. Gross, Chem. Commun. 2000, 1957-1958.
37. R. A. Eikey, S. I. Khan, M. M. Abu-Omar, Angew. Chem. Int. Ed. 2002, 41, 3592-3595.
38. G. Golubkov, Z. Gross, Angew. Chem. Int. Ed. 2003, 42, 4507-4510.
39. L. Simkhovich, I. Goldberg, Z. Gross, Inorg. Chem. 2002, 41, 5433-5439.
40. J. T. Groves, R. Quinn, J. Am. Chem. Soc. 1985, 107, 5790-5792.
41. L. Simkhovich, I. Luobeznova, I. Goldberg, Z. Gross, Chem. Eur. J. 2003, 9, 201-208.
42. a) A. Mahammed, I. Goldberg, Z. Gross, Org. Lett. 2001, 3, 3443-3446;
43. b) L. Simkhovich, P. Iyer, I. Goldberg, Z. Gross, Chem. Eur. J. 2002, 8, 2595-2601;
44. c) I. Saltsman, I. Goldberg, Z. Gross, Tetrahedron Lett. 2003, 44, 5669-5673.
45. For a corrole with chiral moieties, see: B. Andrioletti, E. Rose, J. Chem. Soc. Perkin Trans. 1 2002, 715-716.
46. I. Saltsman, A. Mahammed, I. Goldberg, E. Tkachenko, M. Botoshansky, Z. Gross, J. Am. Chem. Soc. 2002, 124, 7411-7420.