Oxygen-directed, copper-catalyzed, diastereoselective protosilylation of cyclopropenes

Abstract

Herein, we report a copper-catalyzed, oxygen-directed protosilylation of cyclopropenes. This method provides a facile approach to access organosilanes bearing a cyclopropyl group with broad functional group tolerance. The key to the success of this process lies in the use of a monodentate N-heterocyclic carbene as the ligand, which leaves a vacant site on the copper center for coordination with the OH or ester group. Preliminary mechanistic studies reveal that the hydroxyl or ester group not only acts as a directing group (DG) but also significantly enhances reactivity.