Gold‐Catalyzed Reaction of Anthranils with Alkynyl Sulfones for the Regioselective Formation of 3‐Hydroxyquinolines

Abstract

AbstractThe gold‐catalyzed regioselective formation of 3‐hydroxyquinoline is accessed by combining anthranils and alkynyl sulfones. The selective scission of the epoxide intermediate stems from the thermodynamic stability difference of the resultant cation according to quantum chemical calculations. The subsequent semi‐pinacol rearrangement leads to the 1,2‐shift of an aryl or alkyl group originating from the sulfone. A gram‐scale synthesis of 3‐hydroxyquinoline further manifests the viability of the protocol for the preparation of this important scaffold.magnified image