Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H

Abstract

The tremendous success of stereogenic carbon compounds has never ceased to inspire researchers to explore the potentials of stereogenic silicon compounds. Intermolecular C–H silylation thus represents the most versatile and straightforward strategy to construct C–Si bonds, however, its enantioselective variant has been scarcely reported to date. Herein we report a protocol that allows for the enantioselective intermolecular C–H bond silylation, leading to the construction of a wide array of acyclic stereogenic Si–H compounds under simple and mild reaction conditions. Key to the success is (1) a substrate design that prevents the self-reaction of prochiral silane and (2) the employment of a more reactive rhodium hydride ([Rh]-H) catalyst as opposed to the commonly used rhodium chloride ([Rh]-Cl) catalyst. This work unveils opportunities in converting simple arenes into value-added stereogenic silicon compounds.

Abstract

Construction of chiral organosilicon compounds could have implications in photophysical, biological, and chemical fields, as silicon is isoelectronic with carbon, and can mimic carbon atoms while providing slightly different properties. Here the authors present an intermolecular, enantioselective C–H silylation of heterocycles via rhodium catalysis.