Catalytic Oxidation of Saturated C—H Bonds by Tetrabutylammonium Periodate and Manganese Porphyrins

Abstract

Arylalkanes and cycloalkanes are oxidized to their corresponding alcohols and ketones with tetra-n-butylammonium periodate in the presence of manganese(III) porphyrin catalysts and imidazole in CH₂Cl₂, with low to high yields and moderate to high selectivities at ambient temperature.

References

1. (a) R. A. Sheldon and J. K. Kochi, Metal-Catalyzed Oxidation of Organic Compounds, Academic Press, New York and London, 1981, 340; (b) C. L. Hill, Activation and Functionalization of Alkanes, Wiley, New York, 1989; (c) G. W. Parshall and S. D. Ittel SD, Homogeneous Catalysis, 2nd edn., Wiley-Interscience, New York, 1992, ch. 10; (d) D. H. R. Barton and D. Doller, Acc. Chem. Res., 1992, 25, 504; (e) B. A. Arndtsen, R. G. Bergman, T. Andre Mobley and T. H. Peterson, Acc. Chem. Res., 1995, 28, 154; (f) A. Bottcher, M. W. Grinstaff, J. A. Labinger and H. B. Gray, J. Mol. Catal., 1996, 113, 191.
2. (a) T. J. McMurry and J. T. Groves, Cytochrome P-450, Structure, Mechanism and Biochemistry, ed. P. R. Ortiz de Montellano, Plenum Press, New York and London, 1986, ch. 1; (b) B. Meunier, Bull. Soc. Chim., Fr., 1986, 4, 578; (c) D. Mansuy, Pure Appl. Chem., 1987, 59, 759; (d) I. Tabushi, Coord. Chem. Rev., 1988, 86, 1; (e) B. Meunier, Chem. Rev., 1992, 92, 1411; (f) D. Mansuy, Coord. Chem. Rev., 1993, 125, 129; (g) J. P. Collman, X. Zhang, V. J. Lee, E. S. Uffelman and J. I. Brauman, Science, 1993, 261, 1404; (h) P. Bhyrappa, J. K. Young, J. S. Moore and K. S. Suslick, J. Mol. Catal., 1996, 113, 109; (i) A. M. d'A. R. Gonsalves and M. M. Pereira, J. Mol. Catal., 1996, 113, 209; (j) A. Maldotti, A. Molinari, P. Pergamini, R. Amadelli and D. Mansuy, J. Mol. Catal., 1996, 113, 147; (k) D. Dolphin, T. G. Traylor and L. Y. Xie, Acc. Chem. Res., 1997, 30, 251.
3. Abbreviations used include Buⁿ₄ NIO₄, tetra-n-butylammonium periodate; Im, imidazole; TPP, meso-tetraphenylporphyrin dianion; TNP, meso-tetrakis(1-naphthyl)porphyrin dianion; TMP, meso-tetramesitylporphyrin dianion; TPFPP, meso-tetrakis(penta-fluorophenyl)porphyrin dianion; TDCPP, meso-tetrakis (2,6-dichlorophenyl)porphyrin dianion.
4. (a) D. Mohajer and S. Tangestaninejad, J. Chem. Soc., Chem. Commun., 1993, 240; (b) D. Mohajer and S. Tangestaninejad, Tetrahedron Lett., 1994, 35, 945.
5. (a) J. T. Groves, W. J. Kruper, Jr. and R. C. Hawshatter, J. Am. Chem. Soc., 1980, 102, 6375; (b) C. L. Hill and B. C. Schardt, J. Am. Chem. Soc., 1980, 102, 6374; (c) R. D. Arasasingham, G. X. He and T. C. Bruice, J. Am. Chem. Soc., 1993, 115, 7985.
6. M. F. Powell, E. F. Pai and T. C. Bruice, J. Am. Chem. Soc., 1984, 106, 3277.