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Catalyst-free Conjugated Addition of Thiols to Alpha,beta-unsaturated Carbonyl Compounds in Water

Overview
Journal Org Lett
Specialties Biochemistry
Chemistry
Date 2006 May 19
PMID 16706544
Citations 16
Authors
Affiliations
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Abstract

[reaction: see text] Catalyst-free conjugate addition of thiols to alpha,beta-unsaturated carbonyl compounds in water is reported. beta-Sulfido carbonyl compounds were formed at room temperature, in short times and with excellent chemoselectivity. Competitive dithiane/dithiolane formation, transesterification, and ester cleavage were not observed. Water played a dual role in simultaneously activating the alpha,beta-unsaturated carbonyl compound and the thiol. This new methodology constitutes an easy, highly efficient, and green synthesis of beta-sulfido carbonyl compounds.

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