Oxygen-Deletion Skeletal Editing of Oxetanes to Cyclopropanes

Abstract

Oxetanes and cyclopropanes are privileged small strained rings with widespread applications in molecular design. Conceptually, deletion of the oxygen atom from an oxetane would provide a direct route to cyclopropanes, but such a transformation has remained elusive. Here we report an oxygen-deletion skeletal editing strategy that converts readily available oxetanes into cyclopropanes through a one-pot deconstructive–reconstructive sequence involving dibrominative ring opening and electroreductive cyclization. The method exhibits a broad substrate scope, tolerates diverse functional groups, and enables late-stage editing of complex molecules.