Ir(III)-Catalyzed Tandem Annulation of Aromatic Amides with 1,6-Diynes via Dual C–H Bond Activation

An Ir(III)-catalyzed annulation of aryl amides with 1,6-diynes <i>via ortho-</i> as well as <i>meta</i>-dual C-H bond activation reaction is reported. The scope of the annulation reaction was examined with various substituted aryl amides, as well as 1,6-diynes. In this protocol, 1,6-diynes exhibit diverse reactivity compared with internal alkynes. It is important to note that the three C-C bond formation takes place consecutively <i>via ortho</i> followed by <i>meta</i>-dual C-H bond annulation by using a weak chelating group in one pot. A possible catalytic reaction mechanism was proposed to account for the annulation reaction.