Alkyl Carbazates for Electrochemical Deoxygenative Functionalization of Heteroarenes.

The C-O bond cleavage for activation of alcohols is synthetically useful and practically challenging. This work describes carbazate as a new type of electrochemically activated alkylating agent derived from ubiquitous alcohols for direct functionalization of heteroarenes under mild electrolytic conditions. The simple undivided cell at low oxidative potentials with carbon/platinum electrode set-ups offers excellent substrate tolerance, affording a variety of primary, secondary and tertiary alkyl-decorated heterocycles in good chemical yields. Furthermore, the mechanism for this electrochemical deoxyalkylation reaction has been investigated.