A palladium-catalyzed [4 + 1] annulation of Narylimidoyl chlorides with β-keto esters has been developed. In the presence of Pd(OAc) 2 , PCy 3 , and K 3 PO 4 , a variety of fluoalkylcontaining 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.