Organic Base-Facilitated Thiol–Thioalkyne Reaction with Exclusive Regio- and Stereoselectivity

Abstract

Here, we report the regiospecific hydrothiolation of electron-rich thioalkynes with exclusive stereoselectivity facilitated by an organic base, which could proceed exceedingly fast under ambient atmosphere and room temperature, affording β trans addition products in up to nearly quantitative yields. The dual nature of the sulfur atom in attracting and donating electrons is supposed to be pivotal in determining the regio-and stereoselectivity. This system tolerates a wide range of thiols and thioalkynes and shows great potential in polymer synthesis.