Electrochemical synthesis of enaminones via a decarboxylative coupling reaction

Abstract

An environmentally benign and efficient electrochemical synthesis of enaminones via a decarboxylative coupling reaction of α-keto acids using n-Bu₄NI as a redox catalyst and electrolyte under constant current electrolysis in an undivided cell is reported. A broad vinyl azide substrate scope and high functional group tolerance are observed. A gram-scale reaction further demonstrates the practicability of the protocol. The results of cyclic voltammetry and control experiments indicate that I₂ is likely the active species to initiate the oxidative decarboxylation via an acyl hypoiodite intermediate.