A Convenient Late‐Stage Fluorination of Pyridylic C−H Bonds with N‐Fluorobenzenesulfonimide. (6th October 2016)

• Record Type: Journal Article
• Authors: Meanwell, Michael; Nodwell, Matthew B.; Martin, Rainer E.; Britton, Robert
• Is Part Of: Angewandte Chemie. Volume 128:Number 42(2016)
• Page Start: 13438
• Page End: 13442
• Publication Date: 2016-10-06
• Subjects: Fluorierungen -- Medizinische Chemie -- N-Fluorbenzolsulfonimid -- Pyridine -- Späte Funktionalisierung; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201606323
• Languages: English
• ISSNs: 0044-8249

Abstract

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.