Ionic Liquid Promoted Regio- and Stereo-Selective Thiolysis of Epoxides—A Simple and Green Approach to β-Hydroxy- and β-Keto Sulfides

A variety of epoxides underwent facile cleavage by thiols under the catalysis of 1-methyl-3-butylimidazolium bromide, [bmIm]Br, to produce the corresponding β-hydroxy sulfides with high regio- and stereo-selectivity. On the other hand, a specially designed basic ionic liquid, [bmIm]OH, efficiently catalyzes the thiolysis of α,β-epoxy ketones providing β-keto sulfides through simultaneous retro-aldol cleavages. The reactions are clean, high yielding, and do not require any organic solvent. The catalyst is also recycled.