An innovative 1,5-HAT cascade strategy has been advanced for the nickel-catalyzed distal arylation via cross-electrophile coupling. Through specific migration, the remote C(sp3)-H bond is regioselectively activated, and Ar-I as the available electrophile is used for the construction of the C(sp3)-C(sp2) bond. This method also has broad applicability for benzylic and aliphatic N-fluorocarboxamides with yields up to 80%. Furthermore, a series of control experiments demonstrated that this reaction is probably initiated by a radical process.