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Liu, Xinfei; Ye, Xinyi; Bureš, Filip; Liu, Hongjun; Jiang, Zhiyong
Angewandte Chemie (International ed.), September 21, 2015, Letnik: 54, Številka: 39Journal Article
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. Radical control: A radical mechanism for N‐tetrahydroisoquinolines (THIQ) in the presence of oxygen was successfully accomplished by employing a dicyanopyrazine‐derived chromophore (DPZ) as a photoredox catalyst. The substrates can undergo either addition‐cyclization, addition‐elimination, addition‐coupling, or addition‐protonation by judiciously regulating the reaction conditions. Four types of N‐heterocycles are generated in moderate to excellent yields.
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