A palladium-catalyzed [4 + 1] annulation of N-arylimidoyl chlorides with β-keto esters has been developed. In the presence of Pd(OAc)2, PCy3, and K3PO4, a variety of fluoalkyl-containing N-arylimidoyl chlorides smoothly underwent the cascade C-H imidoylation/deacylative Heck-type reactions to afford biologically important 2-fluoroalkyl indoles in moderate to good yields.