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

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 (O2). In alcoholic
solvents, decarboxylation occurs at room temperature to provide a
1,1-difunctionalized 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.