A Pd(II)-catalyzed C(sp3)-H/C(sp2)-H coupling/annulation of anilides and α-dicarbonyl compounds for the synthesis of diverse N-acyl indoles is described. The reaction is achieved by cascade C-H activation, coupling, and intramolecular cyclization. This protocol provides a variety of indoles with high functional group tolerance and excellent regioselectivity. The utility of this protocol is demonstrated by transforming the synthesized compound into diversely functionalized analogues.