Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 25, Pages 9342-9345Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja4047125
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Funding
- Welch Foundation [E-1571]
- National Institute of General Medical Science [R01GM077635]
- Camille and Henry Dreyfus Foundation
- Norman Hackerman Advanced Research Program
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We have developed a method for direct, copper-catalyzed, auxiliary-assisted fluorination of beta-sp(2) C-H bonds of benzoic acid derivatives and gamma-sp(2) C-H bonds of alpha,alpha-disubstituted benzylamine derivatives. The reaction employs a CuI catalyst, a AgF fluoride source, and DMF, pyridine, or DMPU solvent at moderately elevated temperatures. Selective mono- or difluorination can be achieved by simply changing reaction conditions. The method shows excellent functional group tolerance and provides a straightforward way for the preparation of ortho-fluorinated benzoic acids.
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