title: Copper-mediated perfluoroalkylation of heteroaryl bromides with (phen)CuRF.
abstract: The attachment of perfluoroalkyl groups onto organic compounds has been a major synthetic goal over the past several decades. Previously, our group reported phenanthroline-ligated perfluoroalkyl copper reagents, (phen)CuRF, which react with aryl iodides and aryl boronates to form the corresponding benzotrifluorides. Herein the perfluoroalkylation of a series of heteroaryl bromides with (phen)CuCF3 and (phen)CuCF2CF3 is reported. The mild reaction conditions allow the process to tolerate many common functional groups. Perfluoroethylation with (phen)CuCF2CF3 occurs in somewhat higher yields than trifluoromethylation with (phen)CuCF3, creating a method to generate fluoroalkyl heteroarenes that are less accessible from trifluoroacetic acid derivatives.
authors.affiliation: University of California , Department of Chemistry, Berkeley, California 94720, United States.
authors.forename: Michael G
authors.initials: MG
authors.lastname: Mormino
authors.forename: Patrick S
authors.initials: PS
authors.lastname: Fier
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig
mesh_terms: D000478:Alkylation; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D006842:Hydrocarbons, Brominated; D006845:Hydrocarbons, Fluorinated; D003300:Copper