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A Convenient Late‐Stage Fluorination of Pyridylic C−H Bonds with N ‐Fluorobenzenesulfonimide
Author(s) -
Meanwell Michael,
Nodwell Matthew B.,
Martin Rainer E.,
Britton Robert
Publication year - 2016
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.201606323
Subject(s) - lipophilicity , pyridine , metabolic stability , chemistry , selectivity , combinatorial chemistry , fluorine , halogenation , medicinal chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , in vitro
Pyridine features prominently in pharmaceuticals and drug leads, and methods to selectively manipulate pyridine basicity or metabolic stability are highly sought after. A robust, metal‐free direct fluorination of unactivated pyridylic C−H bonds was developed. This convenient reaction shows high functional‐group tolerance and offers complimentary selectivity to existing C−H fluorination strategies. Importantly, this late‐stage pyridylic C−H fluorination provides opportunities to rationally modulate the basicity, lipophilicity, and metabolic stability of alkylpyridine drugs.