Nickel-Catalyzed Claisen Condensation Reaction between Two Different Amides.

A nickel-catalyzed Claisen condensation reaction between two amides, where one possesses an α-proton, for the synthesis of β-ketoamides was developed. Ni(glyme)Cl2 and terpyridine serve as the active catalysts in the presence of Mn and LiCl. N,N-Methylphenyl and N,N-diphenyl benzamide derivatives react with cyclic and noncyclic amides to give their corresponding β-ketoamides in moderate to good yields. In addition, a DFT calculation suggests that reductive elimination is the rate-determining step.