title: N-Acylsaccharins: Stable Electrophilic Amide-Based Acyl Transfer Reagents in Pd-Catalyzed Suzuki-Miyaura Coupling via N-C Cleavage.
abstract: The development of efficient catalytic methods for N-C bond cleavage in amides remains an important synthetic challenge. The first Pd-catalyzed Suzuki-Miyaura cross-coupling of N-acylsaccharins with boronic acids by selective N-C bond activation is reported. The reaction enables preparation of a variety of functionalized diaryl and alkyl-aryl ketones with broad functional group tolerance and in good to excellent yields. Of general interest, N-acylsaccharins serve as new, highly reactive, bench-stable, economical, amide-based, electrophilic acyl transfer reagents via acyl-metal intermediates. Mechanistic studies strongly support the amide N-C(O) bond twist as the enabling feature of N-acylsaccharins in the N-C bond cleavage.
authors: Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
authors: Chengwei
authors: C
authors: Liu
authors: Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
authors: Guangrong
authors: G
authors: Meng
authors: 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: Yongmei
authors: Y
authors: Liu
authors: College of Chemistry and Chemical Engineering, Yangzhou University , 180 Siwangting Road, Yangzhou 225002, China.
authors: Ruzhang
authors: R
authors: Liu
authors: Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
authors: Roger
authors: R
authors: Lalancette
authors: Department of Chemistry, Wroclaw University , F. Joliot-Curie 14, Wroclaw 50-383, Poland.
authors: Roman
authors: R
authors: Szostak
authors: Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
authors: Michal
authors: M
authors: Szostak