title: Copper-mediated difluoromethylation of aryl and vinyl iodides.
abstract: Selectively fluorinated molecules are important as materials, pharmaceuticals, and agrochemicals, but their synthesis by simple, mild, laboratory methods is challenging. We report a straightforward method for the cross-coupling of aryl and vinyl iodides with a difluoromethyl group generated from readily available reagents to form difluoromethylarenes  and difluoromethyl-substituted alkenes. The reaction of electron-neutral, electron-rich, and sterically hindered aryl and vinyl iodides with the combination of CuI, CsF and TMSCF(2)H leads to the formation of difluoromethyl-substituted products in high yield with good functional group compatibility. This transformation is surprising, in part, because of the prior observation of the instability of CuCF(2)H.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, United States.
authors.forename: Patrick S
authors.initials: PS
authors.lastname: Fier
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D054879:Halogenation; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents / Q000138:chemical synthesis / Q000737:chemistry; D007454:Iodides / Q000138:chemical synthesis / Q000737:chemistry*; D008745:Methylation
chemical_list: D000475:Alkenes; D006841:Hydrocarbons, Aromatic; D007202:Indicators and Reagents; D007454:Iodides; D003300:Copper