Palladium-catalyzed cyclizative cross coupling of ynone oximes with 2-haloaryl N-acrylamides for isoxazolyl indoline bis-heterocycles

Abstract

Metal-catalyzed cyclizative cross-coupling reactions have attracted enormous attention due to their unique cascade nature. We demonstrated, herein, a dual-cyclizative coupling of ynone oxime ethers with acrylamides for the synthesis of methylene-linked isoxazolyl 2-oxindoles. The cascade was triggered by a palladium(II)-catalyzed ynone oxime ether cyclization, which underwent a Heck-type coupling intercepted by an aryl iodide insertion. Control experiments were carried out to understand the mechanism.