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Sequential Photoredox Catalysis for Cascade Aerobic Decarboxylative Povarov and Oxidative Dehydrogenation Reactions of N ‐Aryl α‐Amino Acids
Author(s) -
Shao Tianju,
Yin Yanli,
Lee Richmond,
Zhao Xiaowei,
Chai Guobi,
Jiang Zhiyong
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800135
Subject(s) - chemistry , dehydrogenation , photoredox catalysis , catalysis , chromophore , aryl , substituent , amino acid , oxidative phosphorylation , cascade , cascade reaction , combinatorial chemistry , organic chemistry , photochemistry , photocatalysis , alkyl , biochemistry , chromatography
A visible‐light‐driven sequential photoredox catalysis to allow N ‐aryl α‐amino acids to experience efficient cascade aerobic decarboxylative Povarov and oxidative dehydrogenation (ODH) reactions is described. With a dicyanopyrazine‐derived chromophore (DPZ) as a photoredox catalyst in both transformations, two series of valuable azaarenes, i. e., 4‐amino tetrahydroquinolines (THQs) and quinolines, were obtained in satisfactory yields featuring diverse 2‐ and 2,3‐substituent patterns. To enable the ODH reaction of 4‐amino THQs, a cooperative catalysis with N ‐hydroxyphthalimide was developed. Additionally, an unprecedented synthesis of chiral N ‐amino‐2‐methyl THQs with high enantioselectivities was realized.