Nickel-Catalyzed Denitrogenative Cross-Coupling Reaction of 1,2,3-Benzotriazin-4(3H)‑ones with Organoboronic Acids: An Easy Access to Ortho-Arylated and Alkenylated Benzamides

A novel nickel-catalyzed approach to synthesize ortho-arylated and alkenylated benzamides in good to high yields via a denitrogenative cross-coupling reaction of 1,2,3-benzotriazin-4­(3H)-ones with organoboronic acids is described. The reaction proceeds through a five-membered azanickelacyclic intermediate with the extrusion of a nitrogen molecule. Moreover, the resulting ortho-arylated benzamides were successfully converted into synthetically useful substituted fluorenones and ortho-arylated benzylamine derivatives in high yields.