Transition-Metal-Catalyzed Addition/Cyclization Reactions of the C-N Multiple Bonds Containing Species.

This article describes our research work for the past decade, which involves the transition-metal-catalyzed cyclization reactions of the C-N multiple bonds containing species and their synthetic applications to access various heterocyclic compounds. The concepts of reactions including four types of coupling with a subsequent cyclization are (1) the transition-metal performs as a Lewis acid to activate a nitrile and accelerate the nucleophilic addition, (2) the transition-metal-catalyzed 1,2-insertion reaction of nitrile, (3) the Cu-catalyzed C-N coupling reaction of imine, and (4) the Co-catalyzed addition/cyclization reaction of imine. These methods can be used to synthesize various N-containing aromatic heterocycles with higher efficiency, and can be applied to the synthesis of relevent natural alkaloids, their derivatives as well as biologically active compounds.