Room-Temperature C–C Bond Cleavage and Ring Expansion of Benzene by a Copper(I)-Substituted Silylene

Abstract

Abstract The cleavage and functionalization of benzene C–C bonds under mild conditions is of fundamental interest yet remains challenging. Herein, we report that an in situ generated copper(I)-substituted silylene undergoes reversible insertion into benzene at room temperature, affording a silepin with a reactive Cu–Si bond. This metal–silicon linkage enables diverse substitutions (H, halogen, alkyl, allyl, allenyl, propargyl) through facile cleavage, offering a mild strategy for benzene ring expansion and functionalization.