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Synthesis 2003(12): 1875-1877
DOI: 10.1055/s-2003-40981
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© Georg ThiemeVerlag Stuttgart · New York

N-Bromosuccinimideand Iodine Catalyzed Highly Efficient Deoxygenation ofSulfoxides to Thioethers Using 3-Mercaptopropionic Acid under Mild ReactionConditions

Babak Karimi*, Daryoush Zareyee
Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), P.O. Box 45195-159,GavaZang, Zanjan, Iran
Fax: +98(241)4249023; e-Mail: karimi@iasbs.ac.ir;
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Publication History

Received 12 March 2003
Publication Date:
30 July 2003 (online)

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Abstract

A variety of alkyl and aryl sulfoxides have been successfullydeoxygenated using 3-mercaptopropionic acid as a reducing agentand a catalytic amount of either NBS or I2 (5-10mol%) in MeCN at ambient temperature. Under the describedreaction condition, acid sensitive substrates such as acetals remainedintact after several hours.

Key words

sulfoxides - deoxygenation - thioether - catalysis