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Copper-Catalyzed, Directing Group-Assisted Fluorination of Arene and Heteroarene C–H Bonds

Author:
Truong, Thanh, Klimovica, Kristine, Daugulis, Olafs
Source:
Journal of the American Chemical Society 2013 v.135 no.25 pp. 9342-9345
ISSN:
1520-5126
Subject:
benzoic acid, catalysts, chemical bonding, copper, fluorides, pyridines, solvents, temperature
Abstract:
We have developed a method for direct, copper-catalyzed, auxiliary-assisted fluorination of β-sp² C–H bonds of benzoic acid derivatives and γ-sp² C–H bonds of α,α-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.
Agid:
5388767