A Copper-Mediated Radical α-Heteroarylation of Nitriles with Azobis(alkylcarbonitriles).

Abstract

A new practical method has been developed for the α-heteroarylation of aliphatic nitriles with heteroarenes and azobis(alkylcarbonitriles) using Cu(OAc)2 as an oxidizing agent. This method allows the easy construction of nitrile-, aryl-, and dialkyl-bearing quaternary carbon centers from readily available building blocks, without requiring prefunctionalization steps. This reaction is based on adding cyanodialkyl radicals onto heteroarenes, including benzofurans, furans, pyrroles, and indoles. The resulting α-heteroaryl nitriles are useful synthetic intermediates and pharmacophores in biologically active molecules.