Deoxyfluorination of Carboxylic Acids via an In Situ Generated Trifluoromethoxide Salt

An in situ generated pyridinium trifluoromethoxide salt (PyOCF3) is a highly effective deoxyfluorination reagent for the synthesis of acid fluorides. PyOCF3 is formed at room temperature from the reaction of 2,4-dinitro­(trifluoromethoxy)­benzene with 4-dimethylaminopyridine. PyOCF3 undergoes slow r...

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Bibliographic Details
Published in:Organic letters 2023-12, Vol.25 (50), p.9025-9029
Main Authors: Lisboa, Al Vicente Riano D., Duran-Camacho, Geraldo, Ehrlacher, Annika K., Lasky, Matthew R., Sanford, Melanie S.
Format: Article
Language:English
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Summary:An in situ generated pyridinium trifluoromethoxide salt (PyOCF3) is a highly effective deoxyfluorination reagent for the synthesis of acid fluorides. PyOCF3 is formed at room temperature from the reaction of 2,4-dinitro­(trifluoromethoxy)­benzene with 4-dimethylaminopyridine. PyOCF3 undergoes slow release of fluorophosgene and fluoride, which serve as the electrophile and nucleophile, respectively, for deoxyfluorination. A wide substrate scope and high functional group tolerance are demonstrated. Furthermore, the acid fluorides can be purified by filtration and telescoped to various known reactions.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c03706