Dibromomethane-Triggered Electrochemical Cyclization of Enaminones with Amidines for the Synthesis of 5-Acylimidazoles

J Org Chem. 2024 Dec 20;89(24):18565-18570. doi: 10.1021/acs.joc.4c02507. Epub 2024 Nov 29.

Abstract

An electrochemical tandem cyclization of enaminones with amidines has been reported for the first time using dibromomethane as an initiating agent in an undivided cell. Following this protocol, a vast variety of polysubstituted 5-acylimidazoles were obtained in moderate to good yields without the use of external oxidants. Mechanistic studies indicate that the bromide anion, electroreductively generated from dibromomethane, acts as a redox mediator to complete the catalytic cycle.