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.

Division of Chemistry and Biological Chemistry Nanyang Technological University 21 Nanyang Link 637371

Institute of Organic Chemistry and Technology University of Pardubice Faculty of Chemical Technology Studentská 573 Pardubice 53210

Key Laboratory of Natural Medicine and Immuno Engineering of Henan Province Henan University Jinming Campus Kaifeng Henan 475004

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Structural elaboration of dicyanopyrazine: towards push-pull molecules with tailored photoredox activity