A nickel(II)-catalyzed alkynylation/annulation cascade via double C-H cleavage has been successfully achieved. This methodology adopted a removable N,O-bidentate directing group with a broad range of amide substrates and terminal alkynes being well tolerated. The catalytic system allowed for atom-economical and environmentally benign one-pot construction of the corresponding 3-methyleneisoindolin-1-one derivatives using O2 as the external oxidant.