title: 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 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 straightforward way for the preparation of ortho-fluorinated benzoic acids.
authors.affiliation: Department of Chemistry, University of Houston, Houston, Texas 77204-5003, United States.
authors.forename: Thanh
authors.initials: T
authors.lastname: Truong
authors.forename: Kristine
authors.initials: K
authors.lastname: Klimovica
authors.forename: Olafs
authors.initials: O
authors.lastname: Daugulis
mesh_terms: D019817:Benzoic Acid / Q000737:chemistry*; D001596:Benzylamines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D054879:Halogenation; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D001596:Benzylamines; D009942:Organometallic Compounds; D003300:Copper; D019817:Benzoic Acid; C030796:benzylamine