Rhodium-Catalyzed Enantioselective Intermolecular C–H Silylation of Simple Arenes: Synergistic Substituent Effects Overcome Silane Redistribution to Enable Synthesis of Si-Stereogenic Arylsilanes

Abstract

The non-directed intermolecular C–H bond silylation has manifested itself as a versatile tool for the access of organosilicon compounds, however the corresponding asymmetric transformations remain elusive primarily due to the facile self-reactions of silane reactants. Herein we disclose an efficient protocol that involves steric-hindrance enabled, Rh-catalyzed enantioselective intermolecular C–H bond silylation of simple arenes to deliver a broad array of Si-stereogenic monohydrosilanes in good yields with excellent enantioselectivities (up to 99% ee), featuring readily available starting materials, simple synthetic operations and mild reaction conditions.