title: Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of N-Mesylamides by N-C Cleavage: Electronic Effect of the Mesyl Group.
abstract: 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.
authors.affiliation: Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
authors.forename: Chengwei
authors.identifier: 0000-0003-1297-7188
authors.initials: C
authors.lastname: Liu
authors.affiliation: Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.|College of Chemistry and Chemical Engineering, Yangzhou University , 180 Siwangting Road, Yangzhou 225002, China.
authors.forename: Yongmei
authors.initials: Y
authors.lastname: Liu
authors.affiliation: College of Chemistry and Chemical Engineering, Yangzhou University , 180 Siwangting Road, Yangzhou 225002, China.
authors.forename: Ruzhang
authors.initials: R
authors.lastname: Liu
authors.affiliation: Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
authors.forename: Roger
authors.initials: R
authors.lastname: Lalancette
authors.affiliation: Department of Chemistry, Wroclaw University , F. Joliot-Curie 14, Wroclaw 50-383, Poland.
authors.forename: Roman
authors.initials: R
authors.lastname: Szostak
authors.affiliation: Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
authors.forename: Michal
authors.identifier: 0000-0002-9650-9690
authors.initials: M
authors.lastname: Szostak