Synlett 2004(7): 1239-1242  
DOI: 10.1055/s-2004-825583
LETTER
© Georg Thieme Verlag Stuttgart · New York

Indium(I) Iodide-Promoted Cleavage of Dialkyl Disulfides and Subsequent Michael Addition of Thiolate Anions to Conjugated Carbonyl Compounds

Brindaban C. Ranu*, Tanmay Mandal
Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta - 700 032, India
Fax: +91(33)24732805; e-Mail: ocbcr@iacs.res.in;
Further Information

Publication History

Received 23 March 2004
Publication Date:
10 May 2004 (online)

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Abstract

Indium(I) iodide promotes cleavage of dialkyl disulfides generating thiolate anions which then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters and nitriles under neutral conditions producing corresponding β-keto or β-cyano sulfides in high yields. There are several examples of dialkyl/diaryl disulfides and activated alkenes participating in this reaction.