A mild, efficient and selective oxidation of sulfides to sulfoxides

Abstract

Several titanium derivatives supported on silica have been investigated as catalysts in the sulfide→sulfoxide oxidation; the supported titanium/tartaric acid catalyst is highly suited to reactions carried out with H₂O₂, leading to high yields and high sulfoxide/sulfone selectivities, while small asymmetric inductions (up to 13%) are observed.

References

1. J. Drabowski, P. Kielbasinski and M. Mikolajczyk, Synthesis of Sulfoxides, Wiley, New York, 1994; M. Madesclaire, Tetrahedron, 1986, 42, 549.
2. G. W. Breton, J. D. Fields and P. J. Kropp, Tetrahedron Lett., 1995, 36, 3825; P. Kannan, R. Sevvel, S. Rajagopal and K. Pitchumani, Tetrahedron, 1997, 53, 7635; R. S. Varna, R. K. Saini and H. M. Meshram, Tetrahedron Lett., 1997, 38, 6525; M. H. Ali and W. C. Stevens, Synthesis, 1997, 764; M. Hirano, S. Yakabe, S. Itoh, J. H. Clark and T. Morimotoa, Synthesis, 1997, 1161; V. Hulea, P. Moreau and F. di Renzo, J. Mol. Catal. A, 1996, 111, 355.
3. R. S. Reddy, J. S. Reddy, R. Kumar and P. Kumar, J. Chem. Soc., Chem. Commun., 1992, 84.
4. P. S. Raglavan, V. Ramaswamy, T. T. Upadhya, A. Sudalai, A. V. Ramaswamy and S. Sivasankar, J. Mol. Catal. A, 1997, 122, 75.
5. S. V. N. Raju, T. T. Upadhya, S. Ponatnam, T. Daniel and A. Sudalai, Chem. Commun., 1996, 1969.
6. A. Corma, M. Iglesias and F. Sánchez, Catal. Lett., 1996, 39, 153.
7. R. A. Sheldon, in Aspects of Homogeneous Catalysis, ed. R. Ugo, Reidel, Dordrecht, 1981, vol. 4, pp. 1–70.
8. C. Cativiela, J. M. Fraile, J. I. García and J. A. Mayoral, J. Mol. Catal. A, 1996, 112, 259.
9. M. Deshmukh, E. Duñach, S. Juge and H. B. Kagan, Tetrahedron Lett., 1984, 25, 3467.
10. K. Mislow, M. M. Green, P. Laur, J. T. Melillo, T. Simmons and A. L. Ternay Jr., J. Am. Chem. Soc., 1965, 87, 1958.