Metal-Free Transamidation of Secondary Amides via Selective N-C Cleavage under Mild Conditions

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 transamidation of secondary amides under mild conditions. constitutes a two-step procedure to accomplish a Challenging