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Redox‐Divergent Synthesis of Fluoroalkylated Pyridines and 2‐Pyridones through Cu‐Catalyzed N−O Cleavage of Oxime Acetates
Author(s) -
Bai Dachang,
Wang Xueli,
Zheng Guangfan,
Li Xingwei
Publication year - 2018
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.201802311
Subject(s) - oxime , chemistry , redox , catalysis , selectivity , cleavage (geology) , medicinal chemistry , organic chemistry , combinatorial chemistry , geotechnical engineering , fracture (geology) , engineering
Cu‐catalyzed redox‐divergent [3+3] coupling of oxime esters with β‐CF 3 enones and acrylates is described. This redox‐neutral coupling with enones and acrylates affords trifluoromethylated pyridines and pyridones, respectively. Under reductive conditions, difluoromethylated pyridines, difluoromethlated pyridones, and trifluoromethylated dihydropyridones are obtained. The reactions occur under mild conditions with broad substrate scope and regio/redox selectivity.