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

• DOI: 10.1021/acs.joc.3c02036
• Publication Date: 2023-11-15T04:53:43Z
• Authors: Raju Mandal; Subhendu Ghosh; Tamanna Khandelia; Pritishree Panigrahi; Bhisma K. Patel
• Keywords: Decarboxylation; Synthon; Dimethyl carbonate; Base (topology)

A base-mediated 1,1-difunctionalization of vinylene carbonate has been achieved using two different nucleophiles, namely, thiol and alcohol, with the assistance air (O2). In alcoholic solvents, decarboxylation occurs at room temperature to provide a 1,1-difunctionalized product, where serves as an ethynol (C2) synthon in this three-component reaction. On other hand, acetonitrile, exclusive hydrothiolation under basic conditions temperature. This method offers one-pot decarboxylative regioselective difunctionalization for construction α-alkoxy-β-hydroxy sulfide.