Transition-Metal-Free Cyclization of Propargylic Alcohols with Aryne: Synthesis of 3-Benzofuranyl-2-oxindole and 3-Spirooxindole Benzofuran Derivatives

Abstract

An unprecedented base-mediated cyclization of propargylic alcohols with aryne is reported, providing a novel method for the synthesis of 3-benzofuranyl-2-oxindole and 3-spirooxindole benzofuran scaffolds via a propargyl Claisen rearrangement/cycloaddition pathway. The nature of the substituent on acetylene group of propargylic alcohol influences the outcome of the reaction. The protocol offers a transition-metal-free and operationally simple methodology with broad substrate scope as a ready access to complex oxindole-linked heterocyclic compounds.