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Selective C-H Fluorination of Pyridines and Diazines Inspired by a Classic Amination Reaction

Selective C-H Fluorination of Pyridines and Diazines Inspired by a Classic Amination Reaction

Patrick S Fier, John F Hartwig

Science. 2013 Nov 22;342(6161):956-60.

PMID: 24264986

Abstract:

Fluorinated heterocycles are prevalent in pharmaceuticals, agrochemicals, and materials. However, reactions that incorporate fluorine into heteroarenes are limited in scope and can be hazardous. We present a broadly applicable and safe method for the site-selective fluorination of a single carbon-hydrogen bond in pyridines and diazines using commercially available silver(II) fluoride. The reactions occur at ambient temperature within 1 hour with exclusive selectivity for fluorination adjacent to nitrogen. The mild conditions allow access to fluorinated derivatives of medicinally important compounds, as well as a range of 2-substituted pyridines prepared by subsequent nucleophilic displacement of fluoride. Mechanistic studies demonstrate that the pathway of a classic pyridine amination can be adapted for selective fluorination of a broad range of nitrogen heterocycles.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP7783951	Silver(II) fluoride		7783-95-1	Price

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