title: Single-Electron Transmetalation: Synthesis of 1,1-Diaryl-2,2,2-trifluoroethanes by Photoredox/Nickel Dual Catalytic Cross-Coupling.
abstract: Novel methods for the incorporation of fluorinated subunits into organic frameworks are important in pharmaceutical, agrochemical, and materials science applications. Herein, the first method for the cross-coupling of benzylic α-trifluoromethylated alkylboron reagents with (hetero)aryl bromides is achieved through application of a photoredox/nickel dual catalytic system. The harsh conditions and high temperatures required by conventional Suzuki-coupling protocols are avoided by exploitation of an odd-electron pathway that permits room temperature transmetalation of these recalcitrant reagents. This method represents the first direct and general route for the synthesis of unsymmetrical 1,1-diaryl-2,2,2-trifluoroethanes, thereby providing efficient access to a previously unexplored chemical space.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323 (USA).
authors.forename: DaWeon
authors.initials: D
authors.lastname: Ryu
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323 (USA).
authors.forename: David N
authors.initials: DN
authors.lastname: Primer
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323 (USA).
authors.forename: John C
authors.initials: JC
authors.lastname: Tellis
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323 (USA). gmolandr@sas.upenn.edu.
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander
mesh_terms: D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*
chemical_list: D006845:Hydrocarbons, Fluorinated; D007202:Indicators and Reagents; D009532:Nickel; C074585:trifluoroethene
keywords: cross-coupling reactions; dual catalytic systems; organic synthesis; transmetalation; trifluoroethanes