Microwave-promoted regio- and stereoselective vinylation of heterocyclic thiols

Abstract

The first stereoselective vinylation of heterocyclic thiols has been reported. Heterocyclic thiols are shown to react efficiently with activated terminal alkynes in an anti-Markovnikov fashion in absence of any catalyst or additive under microwave irradiation to give Z-selective vinyl sulfides.

An Efficient Catalyst-Free Synthesis of Vinyl Sulfides in Aqueous-Phase

“…The coupling constants of vinyl protons of (Z)-products 8 and 9 are smaller than those of (E)-products, which is consistent with literature reports. 18,23 Table 3. Synthesis of compounds 8 and 9…”