SHORTPAPER	Synthesis 2003: 0335-0336 DOI: 10.1055/s-2003-37349
© Georg Thieme Verlag Stuttgart · New York
Rapid, Efficient and Chemoselective Deoxygenation of Sulfoxides to Thioethers­ Using NaBH4/I2
Babak Karimi*, Daryoush Zareyee
Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), P. O. Box 45195-159, Gava Zang, Zanjan, Iran Fax: +98(241)4249023; e-Mail: karimi@iasbs.ac.ir;
Received 1 October 2002

Abstract

Sodium borohydride in the presence of iodine in anhydrous THF converts a range of structurally different sulfoxides to their thioethers in excellent yields. It has been found that chemoselective deoxygenation of sulfoxides can be achieved in the presence of other reducible functional groups such as esters, nitriles and double bonds.

Key words

sulfoxides - deoxygenation - reduction - NaBH₄ - iodine - sulfides