Reductive Cleavage of the S–Si Bond in Arylsulfanyltrimethylsilanes: a Novel Method for the Synthesis of Unsymmetrical Sulfides†

Abstract

Arylsulfanyltrimethylsilanes are reduced by samarium diiodide to yield samarium arylthiolates which react with alkyl halides to give unsymmetrical sulfides.

References

1. P. Girard, J. L. Namy and H. B. Kagan, J. Am. Chem. Soc., 1980, 102, 2693.
2. G. A. Molander, Chem. Rev., 1992, 92, 29.
3. G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307.
4. X. S. Jia and Y. M. Zhang, Synth. Commun., 1994, 24, 787.
5. G. Solladie, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 6, pp. 133–170.
6. K. Ogura, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 1, pp. 505–539.
7. Y. M. Zhang, Y. P. Yu and W. L. Bao, Synth. Commun., 1995, 25, 1825.
8. J. Q. Wang and Y. M. Zhang, Synth. Commun., 1995, 25, 3545.
9. N. M. Yoon, J. Chei and J. H. Ahn, J. Org. Chem., 1994, 59, 3490.
10. P. Kannan, K. Pitchumani, S. Rajagopal and C. Srinivasan, Chem. Commun., 1996, 369.
11. G. H. Lee, E. B. Choi and C. S. Dak, Tetrahedron Lett., 1994, 35, 2195.