Hydroxylation of alkanes by molecular oxygen with dinuclear Fe^II macrocyclic complexes as catalysts

Abstract

The iron(II) complexes of two new macrocyclic ligands: [24]RBPyBC (L24), a 24-membered macrocycle containing phenol, pyridine and amino donor groups, and [30]RBBPyBC (L30), a 30-membered macrocycle containing phenol, bipyridine, and amino donor groups, were found to be effective for the hydroxylation of alkanes, including cyclohexane and adamantane, with H₂S as a two-electron reductant.

References

1. Z. Wang, J. H. Reibenspies and A. E. Martell, Inorg. Chem., 1997, 36, 629.
2. Z. Wang, Ph.D. Dissertation, Texas A&M University, 1997.
3. Z. Wang and A. E. Martell, Inorg. Chem., submitted.
4. M. P. Woodland, D. S. Patil, R. Cammack and H. Dalton, Biochem. Biophys. Acta, 1986, 873, 237; A. Ericson, B. Hedman, K. O. Hodgson, J. Green, H. Dalton, J. G. Bentsen, R. H. Beer and S. J. Lippard, J. Am. Chem. Soc., 1988, 110, 2330; B. G. Fox, W. A. Froland, J. Dege and J. D. Lipscomb, J. Biol. Chem., 1989, 263, 10023.
5. D. Mansuy, J. F. Bartoli and M. Mometeau, Tetrahedron Lett., 1982, 23, 2781; B. de Poorter, M. Ricci and B. Mounier, Tetrahedron Lett., 1985, 26, 4459; P. Battioni, J. P. Renaud, J. F. Bartoli and D. Mansuy, J. Chem. Soc., Chem. Commun., 1986, 341; J. B. Vincent, J. C. Huffman, G. Christou, Q. Li, M. A. Nanny, D. N. Hendrickson, R. H. Fong and R. H. Fish, J. Am. Chem. Soc., 1988, 110, 6898; R. H. Fish, R. H. Fong, J. B. Vincent and G. Christou, J. Chem. Soc., Chem. Commun., 1988, 1504.
6. E. I. Karasevich, A. M. Khenkin and A. E. Shilov, J. Chem. Soc., Chem. Commun., 1987, 731; P. Battioni, J. F. Bartoli, P. Leduc, M. Fontecave and D. Mansuy, J. Chem. Soc., Chem. Commun., 1987, 791; P. E. Ellis, Jr. and J. E. Lyons, J. Chem. Soc., Chem. Commun., 1989, 1189; P. E. Ellis, Jr. and J. E. Lyons, J. Chem. Soc., Chem. Commun., 1989, 1315.
7. D. H. R. Barton, R. S. Hay-Motherwell and W. B. Motherwell, J. Chem. Soc., Perkin Trans. 1, 1983, 445; D. H. R. Barton, J. Boivin, M. Bastiger, J. Morzyck, R. S. Hay-Motherwell, W. B. Motherwell, N. Ozbalik and K. Schwartzentruber, J. Chem. Soc., Perkin Trans. 1, 1986, 947; C. Balavoine, D. H. R. Barton, J. Boivin, A. Gref, P. L. Coupanec, N. Ozbalik, J. A. X. Pestana and H. Riviere, Tetrahedron, 1988, 44, 1091; D. H. R. Barton, F. Halley, N. Ozbalik, E. Young, G. Balavoin, A. Gref and J. Boivin, New J. Chem., 1989, 13, 177.
8. (a) N. Kitajima, H. Fukui and Y. Moro-oka, J. Chem. Soc., Chem. Commun., 1988, 485; (b) N. Kitajima, M. Ito, H. Fukui and Y. Moro-oka, J. Chem. Soc., Chem. Commun., 1991, 102.