Palladium-Catalyzed Four-Component Cascade Imidoyl-Carbamoylation of Unactivated Alkenes

Abstract

A 1,2-difunctionalization of an unactivated alkene, imidoyl-carbamoylation, has been developed through a palladium-catalyzed four-component cascade reaction involving aryl iodide, alkenyl isocyanide, CO, and amine. Continuous migratory insertion of three different functionalities to the Pd(II) intermediate generated from the previous step takes place in a well-defined sequence. Four chemical bonds, including three C–C bonds and one C–N bond, are formed in this cascade process, leading to a convenient and convergent access to acetamides substituted with five- to seven-membered cyclic ketoimines. In addition, an extra C–N bond is formed through in situ or postreaction cyclization of the amido NH to the ketoimine moiety, providing a facile one-pot access to pyrrolo-fused heterocycles.