Catalyst-free conjugated addition of thiols to α,β-unsaturated carbonyl compounds in water

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.