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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, Email: karimiiasbs.ac.ir

B. Karimi, D. Zareyee, Synthesis, 2003, 335-336.

DOI: 10.1055/s-2003-37349


Abstract

Sodium borohydride in the presence of iodine in anhydrous THF converts various sulfoxides to their thioethers in excellent yields. A chemoselective deoxygenation of sulfoxides can be achieved in the presence of other reducible functional groups such as esters, nitriles and double bonds.

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N-Bromosuccinimide and Iodine Catalyzed Highly Efficient Deoxygenation of Sulfoxides to Thioethers Using 3-Mercaptopropionic Acid under Mild Reaction Conditions

B. Karimi, D. Zareyee, Synthesis, 2003, 1875-1877.


Key Words

deoxygenation of sulfoxides, reduction, sodium borohydride, iodine, sulfides


ID: J66-Y2003-1770