Abstract Reported is the controllable selectivity syntheses of four distinct products from the same starting materials by visible‐light photoredox catalysis. By employing a dicyanopyrazine‐derived chromophore (DPZ) as photoredox catalyst, an aerobic radical mechanism has been developed, and allows the reactions of N ‐tetrahydroisoquinolines (THIQs) with N ‐itaconimides to through four different pathways, including addition‐cyclization, addition‐elimination, addition‐coupling, and addition‐protonation, with satisfactory chemoselectivity. The current strategy provide straightforward access to four different but valuable N‐heterocyclic adducts in moderate to excellent yields.