Au- and Pd-catalyzed cyclization processes: synthesis of polyfunctionalized cyclopropanes

Abstract

Reported herein is an efficient 2-step process involving an Au-catalyzed Prins-type cyclization and a Pd-catalyzed cyclopropane C–H activation for the synthesis of polysubstituted cyclopropanes. Polycyclic heterocycles, effective for C–H activation, are obtained from easily accessible 1,6-enynes and ortho-halide arylaldehydes. Under Pd-catalyzed conditions, these compounds are efficiently transformed into highly functionalized cyclopropanes in moderate to excellent yields. The scalability of these reactions is notable, and mechanistic studies provide insights into the reaction pathways. Furthermore, post-functionalization steps underscore the synthetic versatility of this novel transformation.