Catalyst-Free Conjugated Addition of Thiols to α,β-Unsaturated Carbonyl Compounds in Water
- 1 May 2006
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (11), 2433-2436
- https://doi.org/10.1021/ol060846t
Abstract
Catalyst-free conjugate addition of thiols to α,β-unsaturated carbonyl compounds in water is reported. β-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 α,β-unsaturated carbonyl compound and the thiol. This new methodology constitutes an easy, highly efficient, and green synthesis of β-sulfido carbonyl compounds.Keywords
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