Hydrogen atom abstraction by a high-valent manganese(V)-oxo corrolazine

Inorganic Chemistry

Volumn 45, Issue 13, 2006, Pages 5119-5125

  Lansky, David E ^a   Goldberg, David P ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,4,6 TRI TERT BUTYLPHENOL; 2,4,6-TRI-TERT-BUTYLPHENOL; HYDROGEN; MANGANESE DERIVATIVE; MANGANESE(V) OXO CORROLAZINE; MANGANESE(V)-OXO CORROLAZINE; METALLOPORPHYRIN; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; OXIDATION REDUCTION REACTION; SPECTROSCOPY;

HYDROGEN; KINETICS; MANGANESE COMPOUNDS; METALLOPORPHYRINS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHENOLS; SPECTRUM ANALYSIS;

EID: 33746541220     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic060491+     Document Type: Article

References (41)

1. Meunier, B.; de Visser, S. P.; Shaik, S. Chem. Rev. 2004, 104, 3947-3980.
2. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
3. Fujii, H. Coord. Chem. Rev. 2002, 226, 51-60.
4. McLain, J. L.; Lee, J.; Groves, J. T., Biomimetic Oxygenations Related to Cytochrome P450: Metal-Oxo and Metal-Peroxo Intermediates. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 91-169.
5. Battioni, P.; Renaud, J. P.; Bartoli, J. F.; Reinaartiles, M.; Fort, M.; Mansuy, D. J. Am. Chem. Soc. 1988, 110, 8462-8470.
6. Bernadou, J.; Fabiano, A.-S.; Robert, A.; Meunier, B. J. Am. Chem. Soc. 1994, 116, 9375-9376.
7. Jin, N.; Bourassa, J. L.; Tizio, S. C.; Groves, J. T. Angew. Chem., Int. Ed. 2000, 39, 3849-3851.
8. Jin, N.; Groves, J. T., J. Am. Chem. Soc. 1999, 121, 2923-2924.
9. Palucki, M.; Finney, N. S.; Pospisil, P. J.; Güler, M. L.; Ishida, T.; Jacobsen, E. N., J. Am. Chem. Soc. 1998, 120, 948-954.
10. Khavrutskii, I. V.; Musaev, D. G.; Morokuma, K. Inorg. Chem. 2005, 44, 306-315.
11. Adam, W.; Roschmann, K. J.; Saha-Moller, C. R.; Seebach, D. J. Am. Chem. Soc. 2002, 124, 5068-5073.
12. Yachandra, V. K.; Sauer, K.; Klein, M. P. Chem. Rev. 1996, 96, 2927-2950.
13. Yagi, M.; Kaneko, M. Chem. Rev. 2001, 101, 21-35.
14. Gross, Z.; Golubkov, G.; Simkhovich, L. Angew. Chem., Int. Ed. 2000, 39, 4045-4047.
15. Groves, J. T.; Lee, J.; Maria, S. S. J. Am. Chem. Soc. 1997, 119, 6269-6273.
16. Liu, H. Y.; Lai, T. S.; Yeung, L. L.; Chang, C. K. Org. Lett. 2003, 5, 617-620.
17. Nam, W.; Kim, I.; Lim, M. H.; Choi, H. J.; Lee, J. S.; Jang, H. G. Chem. Eur. J. 2002, 8, 2067-2071.
18. Zhang, R.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 2005, 127, 6573-6582.
19. Lansky, D. E.; Mandimutsira, B.; Ramdhanie, B.; Clausén, M.; Penner-Hahn, J.; Zvyagin, S. A.; Telser, J.; Krzystek, J.; Zhan, R. Q.; Ou, Z. P.; Kadish, K. M.; Zakharov, L.; Rheingold, A. L.; Goldberg, D. P. Inorg. Chem. 2005, 44, 4485-4498.
20. Mandimutsira, B. S.; Ramdhanie, B.; Todd, R. C.; Wang, H. L.; Zareba, A. A.; Czernuszewicz, R. S.; Goldberg, D. P. J. Am. Chem. Soc. 2002, 124, 5170-15171.
21. Eikey, R. A.; Khan, S. I.; Abu-Omar, M. M. Angew. Chem., Int. Ed. 2002, 41, 3592-3595.
22. Kerber, W. D.; Goldberg, D. P. J. Inorg. Biochem. 2006, 100, 838-857.
23. Wang, S. H. L.; Mandimutsira, B. S.; Todd, R.; Ramdhanie, B.; Fox, J. P.; Goldberg, D. P. J. Am. Chem. Soc. 2004, 126, 8-19.
24. Mayer, J. M., Biomimetic Oxygenations Related to Cytochrome P450: Metal-Oxo and Metal-Peroxo Intermediates. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed. Imperial College Press: London, 2000; pp 1-43.
25. Green, M. T.; Dawson, J. H.; Gray, H. B. Science 2004, 304, 1653-1656.
26. Altwicker, E. R. Chem. Rev. 1967, 67, 475-531.
27. IVOH with substrate given the large excess of phenol compared to Mn, we cannot rule out this alternative mechanism.
28. Mahoney, L. R.; DaRooge, M. A. J. Am. Chem. Soc. 1970, 92, 890-899.
29. Snelgrove, D. W.; Lusztyk, J.; Banks, J. T.; Mulder, P.; Ingold, K. U. J. Am. Chem. Soc. 2001, 123, 469-477.
30. Mulder, P.; Saastad, O. W.; Griller, D. J. Am. Chem. Soc. 1988, 110, 4090-4092.
31. Pratt, D. A.; DiLabio, G. A.; Mulder, P.; Ingold, K. U. Acc. Chem. Res. 2004, 37, 334-40.
32. Lucarini, M.; Pedrielli, P.; Pedulli, G. F. J. Org. Chem. 1996, 61, 9259-9263.
33. Mayer, J. M. Acc. Chem. Res. 1998, 31, 441-450.
34. Yiu, D. T. Y.; Lee, M. F. W.; Lam, W. W. Y.; Lau, T. C. Inorg. Chem. 2003, 42, 1225-1232.
35. Gardner, K. A.; Kuehnert, L. L.; Mayer, J. M. Inorg. Chem. 1997, 36, 2069-2078.
36. Estimated from the slope of the plot in Figure 6b of ref 32.
37. Goldsmith, C. R.; Cole, A. P.; Stack, T. D. P. J. Am. Chem. Soc. 2005, 127, 9904-9912.
38. Bordwell, F. G.; Cheng, J. P. J. Am. Chem. Soc. 1991, 113, 1736-1743.
39. For an example of hydrogen-atom abstraction by an iron(III) complex with a similarly low redox potential, see Roth, J. P.; Mayer, J. M. Inorg. Chem. 1999, 38, 2760-2761.
40. Lockwood, M. A.; Blubaugh, T. J.; Collier, A. M.; Lovell, S.; Mayer, J. M. Angew. Chem., Int. Ed. 1999, 38, 225-227.
41. Laarhoven, L. J. J.; Mulder, P.; Wayner, D. D. M. Acc. Chem. Res. 1999, 32, 342-349.