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Organic Base-Facilitated Thiol-Thioalkyne Reaction with Exclusive Regio- and Stereoselectivity
Yunxin Sun1, Ningning Song1, Yanchen Han1
1State Key Laboratory of Organic-Inorganic Composites, College of Chemical Engineering, Beijing University of Chemical Technology, Beijing 100029, China.
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.
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