Base-Induced Decarboxylative 1,1-Alkoxy Thiolation via Hydrothiolation of Vinylene Carbonate

Abstract

A base-mediated 1,1-difunctionalization of vinylene carbonate has been achieved using two different nucleophiles, namely, thiol and alcohol, with the assistance of air (O 2 ). In alcoholic solvents, decarboxylation occurs at room temperature to provide a 1,1difunctionalized product, where vinylene carbonate serves as an ethynol (C2) synthon in this three-component reaction. On the other hand, in acetonitrile, exclusive hydrothiolation occurs under the basic conditions at room temperature. This method offers a one-pot decarboxylative regioselective difunctionalization of vinylene carbonate at room temperature for the construction of α-alkoxy-β-hydroxy sulfide.