Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 64, Pages 15908-15913Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202102854
Keywords
acyloxyphosphonium; carboxylic acids; copper; difluoromethyl ketones; TMSCF3; trifluoromethyl ketones
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Funding
- Loker Hydrocarbon Research Institute
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This method involves the synthesis of trifluoromethyl and difluoromethyl ketones from carboxylic acids using an acyloxyphosphonium ion as the active electrophile, showing tolerance to various functional groups and applicability to late-stage functionalization of pharmaceutical compounds.
A simple and straightforward approach to the synthesis of trifluoromethyl and difluoromethyl ketones from widely available carboxylic acids is disclosed. The transformation utilizes an acyloxyphosphonium ion as the active electrophile, conveniently generated in situ from the carboxylic acid substrate by using commodity chemicals. The utility of the reaction system is exemplified by its chemoselectivity, with tolerance to a variety of important functional groups. The late-stage functionalization of carboxylic acid active pharmaceutical ingredients and pharmaceutically relevant compounds is also discussed.
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