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- Title
A Convenient Late-Stage Fluorination of Pyridylic C−H Bonds with N-Fluorobenzenesulfonimide.
- Authors
Meanwell, Michael; Nodwell, Matthew B.; Martin, Rainer E.; Britton, Robert
- Abstract
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.
- Subjects
PYRIDYL compounds; FLUORINATION; CARBON-hydrogen bonds; FLUOROBENZENE; SULFONAMIDES; IMIDES
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 42, p13438
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201606323