Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 5, Pages 2572-2578Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b12167
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Funding
- Singapore Ministry of Education [R-143-000-A05-112]
- Singapore Agency of Science, Technology and Research (A*STAR) [R-143-000-B09-305]
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Single fluoride substitution in trifluoromethylarenes is an ongoing synthetic challenge that often leads to over-reaction, where multiple fluorides are replaced. Development of this reaction would allow simple access to a vast range of difluoromethyl derivatives of current interest to pharmaceutical, agrochemistry, and materials sciences. Using a catalytic frustrated Lewis pair approach, we have developed a generic protocol that allows a single substitution of one fluoride in trifluoromethyl groups with neutral phosphine and pyridine bases. The resulting phosphonium and pyridinium salts can be further functionalized via nucleophilic substitution, photoredox coupling, and electrophilic transfer reactions allowing the generation of a vast array of difluoromethyl products.
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