A palladium­(II)-catalyzed protocol for inactive β-C­(sp3)–H bond functionalization has been first accomplished. The reaction proceeds through five-membered carbocycles for the formation of C–C bonds via the Pd­(II)/Pd­(IV) cycle. This reaction was carried out with various aryl iodides and benzothiazoles/benzoxazoles/benzimidazoles, which were well-tolerated in this reaction and successfully generated β-C­(sp3)–H arylated products. Further implementation of this batch protocol to continuous flow by utilizing a PTFE (polytetrafluoroethylene) capillary reactor enhanced the reaction efficiency and decreased the reaction time (18.4 min) as compared to batch conditions (8 h). Even on the gram scale, the process produced excellent yield with negligible diarylations. Functional group tolerance, a continuous-flow approach, and easy-to-handle reaction conditions make this inactive β-C­(sp3)–H bond functionalization protocol very attractive.