Electrochemical Cyclization of <i>o</i>-Aminyl Azobenzenes: Roles of Aldehydes in N–N Bond Cleavage

Abstract

Direct functionalization of azobenzenes provides an approach to obtaining valuable molecules in synthetic chemistry. However, an efficient method for the cleavage of the N═N bond of azobenzenes, which is a key process for this transformation, is still lacking. We herein disclose an electrochemical reduction-induced cyclization of azobenzenes with aldehydes via N═N bond cleavage. This electrochemical cyclization of azobenzenes proceeds well in the absence of any transition metals or external chemical oxidants, leading to the formation of N-protected benzimidazoles in moderate to good yields.

Topics & Concepts