title: Metal-Free Transamidation of Secondary Amides via Selective N-C Cleavage under Mild Conditions.
abstract: Nonplanar, electronically destabilized amides have emerged as powerful intermediates in organic synthesis. We report a highly selective method for transamidation of common secondary amides under mild, metal-free conditions that relies on transient N-selective functionalization to weaken amidic resonance. The combination of rational modification of the amide bond with nucleophilic addition mechanism, and the thermodynamic collapse of the resultant tetrahedral intermediate constitutes a two-step procedure to accomplish a challenging transamidation of secondary amides under mild conditions.
authors.affiliation: College of Chemistry and Chemical Engineering, Yangzhou University , 180 Siwangting Road, Yangzhou 225002, China.|Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
authors.forename: Yongmei
authors.initials: Y
authors.lastname: Liu
authors.affiliation: Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
authors.forename: Shicheng
authors.initials: S
authors.lastname: Shi
authors.affiliation: Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
authors.forename: Marcel
authors.initials: M
authors.lastname: Achtenhagen
authors.affiliation: College of Chemistry and Chemical Engineering, Yangzhou University , 180 Siwangting Road, Yangzhou 225002, China.
authors.forename: Ruzhang
authors.identifier: 0000-0002-9569-2622
authors.initials: R
authors.lastname: Liu
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