Publication Date:
2013-11-23
Description:
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.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Fier, Patrick S -- Hartwig, John F -- R37GM-55382/GM/NIGMS NIH HHS/ -- New York, N.Y. -- Science. 2013 Nov 22;342(6161):956-60. doi: 10.1126/science.1243759.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Chemistry, University of California, Berkeley, CA 94720, USA.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/24264986" target="_blank"〉PubMed〈/a〉
Keywords:
Amination
;
Carbon/chemistry
;
Fluorides/chemistry
;
Fluorine/*chemistry
;
*Halogenation
;
Hydrogen/chemistry
;
Hydrogen Bonding
;
Nitrogen/chemistry
;
Pyridines/*chemistry
;
Silver Compounds/chemistry
Print ISSN:
0036-8075
Electronic ISSN:
1095-9203
Topics:
Biology
,
Chemistry and Pharmacology
,
Computer Science
,
Medicine
,
Natural Sciences in General
,
Physics
