Iodine Catalyzed C2-H Formamidation of Quinoline N-Oxides using Isocyanides: A Metal-Free Approach

Abstract

A molecular iodine catalyzed regioselective insertion of isocyanide into C2-H of quinoline N-oxides has been developed. The reaction proceeds through the nucleophilic addition of isocyanide on quinoline Noxides followed by rearrangement in presence of iodine. This metal-free reaction affords rapid access to quinoline 2-formamides with exceptional functional group tolerance, broad substrate scope and 100% atomeconomy. A library of 33 N-(2-quinolinyl)formamides are synthesized, which may find applications in pharmaceuticals and synthetic chemistry.