Chromium-catalyzed couplings of C(aryl)–SMe bonds for accessing arylated and alkylated benzaldehyde derivatives

Abstract

Described here is the chromium-catalyzed cleavage of C(aryl)–SMe bonds leading to coupling with organomagnesium to give functionalized benzaldehydes under mild conditions. This reaction was promoted specifically by a low-cost and simple CrCl₂ salt used as a precatalyst, enabling synchronous activations of ortho-C(aryl)–SMe and ortho′-C(aryl)–H bonds to achieve difunctionalization of benzaldimines. This work provided a strategy for accessing arylated, alkylated, and diarylated benzaldehyde derivatives as a result of the couplings of C(aryl)–SMe and C(aryl)–SMe/C(aryl)–H bonds promoted with cost-effective Cr catalysis.