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Copper‐Catalyzed Deaminative Difluoromethylation
Author(s) -
Zeng Xiaojun,
Yan Wenhao,
Zacate Samson B.,
Cai Aijie,
Wang Yufei,
Yang Dongqi,
Yang Kundi,
Liu Wei
Publication year - 2020
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.202006048
Subject(s) - alkyl , pyridinium , chemistry , bioisostere , catalysis , group (periodic table) , combinatorial chemistry , halide , organic chemistry , medicinal chemistry , chemical synthesis , biochemistry , in vitro
The difluoromethyl group (CF 2 H) is considered to be a lipophilic and metabolically stable bioisostere of an amino (NH 2 ) group. Therefore, methods that can rapidly convert an NH 2 group into a CF 2 H group would be of great value to medicinal chemistry. We report herein an efficient Cu‐catalyzed approach for the conversion of alkyl pyridinium salts, which can be readily synthesized from the corresponding alkyl amines, to their alkyl difluoromethane analogues. This method tolerates a broad range of functional groups and can be applied to the late‐stage modification of complex amino‐containing pharmaceuticals.