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

A novel nickel-catalyzed approach to synthesize <i>ortho</i>-arylated and alkenylated benzamides in good to high yields via a denitrogenative cross-coupling reaction of 1,2,3-benzotriazin-4­(3<i>H</i>)-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 <i>ortho</i>-arylated benzamides were successfully converted into synthetically useful substituted fluorenones and <i>ortho</i>-arylated benzylamine derivatives in high yields.