Iridium(III)-Catalyzed C-H Allylation and Aza-Wacker Cyclization of 2-Aryl Quinazolinones and Vinylcyclopropanes.

Abstract

We describe a sequential protocol for iridium(III)-catalyzed o-C-H (E)-allylation of 2-aryl quinazolinones with vinylcyclopropanes (VCPs), followed by palladium(II)-catalyzed aza-Wacker cyclization and subsequent olefin migration, affording piperidine-fused quinazolinones. A broad substrate scope and complete site selectivity were achieved in this coupling reaction. Furthermore, post-transformations, including Diels-Alder cycloaddition and Michael addition of the synthesized product, underscore the potential of the developed method.