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Controllable Chemoselectivity in Visible‐Light Photoredox Catalysis: Four Diverse Aerobic Radical Cascade Reactions
Author(s) -
Liu Xinfei,
Ye Xinyi,
Bureš Filip,
Liu Hongjun,
Jiang Zhiyong
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201505193
Subject(s) - chemoselectivity , photoredox catalysis , chemistry , protonation , catalysis , chromophore , photochemistry , cascade , selectivity , visible spectrum , combinatorial chemistry , organic chemistry , photocatalysis , materials science , optoelectronics , ion , chromatography
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.