title: Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates.
abstract: Trifluoroethylarenes are found in a variety of biologically active molecules, and strategies for accessing this substructure are important for developing therapeutic candidates and biological probes. Trifluoroethylarenes can be directly accessed via nucleophilic trifluoromethylation of benzylic electrophiles; however, current catalytic methods do not effectively transform electron-deficient substrates and heterocycles. To address this gap, we report a Cu-catalyzed decarboxylative trifluoromethylation of benzylic bromodifluoroacetates. To account for the tolerance of sensitive functional groups, we propose an inner-sphere mechanism of decarboxylation.
authors.affiliation: Department of Medicinal Chemistry, The University of Kansas, Lawrence, Kansas 66045, United States.
authors.forename: Brett R
authors.initials: BR
authors.lastname: Ambler
authors.affiliation: Department of Medicinal Chemistry, The University of Kansas, Lawrence, Kansas 66045, United States.
authors.forename: Lingui
authors.initials: L
authors.lastname: Zhu
authors.affiliation: Department of Medicinal Chemistry, The University of Kansas, Lawrence, Kansas 66045, United States.
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Altman
mesh_terms: D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003653:Decarboxylation; D005463:Fluoroacetates / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D001593:Benzyl Compounds; D005463:Fluoroacetates; D006845:Hydrocarbons, Fluorinated; D003300:Copper