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

Babak Karimi*, Daryoush Zareyee

*Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), P.O. Box 45195-159, GavaZang, Zanjan, Iran, Email: karimiiasbs.ac.ir

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

DOI: 10.1055/s-2003-40981

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Abstract

Various alkyl and aryl sulfoxides have been successfully deoxygenated using 3-mercaptopropionic acid as a reducing agent and a catalytic amount of either NBS or I₂ in MeCN at ambient temperature. Under the described reaction conditions, acid sensitive substrates such as acetals remained intact.

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Rapid, Efficient and Chemoselective Deoxygenation of Sulfoxides to Thioethers Using NaBH₄/I₂

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

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Key Words

deoxygenation of sulfoxides, catalysis, thioethers, 3-mercaptopropionic acid

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ID: J66-Y2003-1920