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Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.

ABSTRACT: We have developed a method for direct, copper-catalyzed, auxiliary-assisted fluorination of ?-sp(2) C-H bonds of benzoic acid derivatives and ?-sp(2) C-H bonds of ?,?-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.

SUBMITTER: Truong T

PROVIDER: S-EPMC3733384 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.

Truong Thanh T Klimovica Kristine K Daugulis Olafs O

Journal of the American Chemical Society 20130612 25

We have developed a method for direct, copper-catalyzed, auxiliary-assisted fluorination of β-sp(2) C-H bonds of benzoic acid derivatives and γ-sp(2) 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 str ...[more]

PMID: 23758609

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