An aryl-to-alkyl radical relay arylation reaction of a remote C(sp3)–H bond using 1,4-dicyanobenzene as an electrochemical redox-mediator†

Abstract

An electroreduction-enabled aryl-to-alkyl radical relay arylation reaction of the remote C(sp³)–H bond of 2-iodoalkylarenes is reported. This electrochemical strategy takes place via a 1,5-H transfer process, leading to various arylated products bearing all-carbon quaternary centers under transition-metal and ligand-free conditions. The aryl nitriles serve as both aryl radical precursors and redox mediators in this transformation.