Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of N‑Mesylamides by N–C Cleavage: Electronic Effect of the Mesyl Group

A general Pd-catalyzed Suzuki–Miyaura cross-coupling of N-mesylamides with arylboronic acids by selective N–C cleavage has been developed. The presented results represent the first example of a transition-metal-catalyzed cross-coupling of amides activated by an atom-economic, cheap, and benign mesyl group. The reaction delivers arylated products featuring a range of useful functional groups by chemoselective cleavage of the amide N–C bond with high efficiency. Both the scope and the origin of high selectivity are discussed. A beneficial effect of the N-mesyl substituent on the bond activation in acyclic amides is presented.