Fluorine-Substituted Arylphosphine for an NHC-Ni(I) System, Air-Stable in a Solid State but Catalytically Active in Solution

Molecules. 2019 Sep 4;24(18):3222. doi: 10.3390/molecules24183222.

Abstract

Monovalent NHC-nickel complexes bearing triarylphosphine, in which fluorine is incorporated onto the aryl groups, have been synthesized. Tris(3,5-di(trifluoromethyl)-phenyl)phosphine efficiently gave a monovalent nickel bromide complex, whose structure was determined by X-ray diffraction analysis for the first time. In the solid state, the Ni(I) complex was less susceptible to oxidation in air than the triphenylphosphine complex, indicating greatly improved solid-state stability. In contrast, the Ni(I) complex in solution can easily liberate the phosphine, high catalytic activity toward the Kumada-Tamao-Corriu coupling of aryl bromides.

Keywords: DFT calculations; Kumada coupling; fluorine-substituted phosphine; intermolecular interaction; monovalent nickel.

MeSH terms

  • Catalysis
  • Coordination Complexes / chemistry*
  • Crystallography, X-Ray
  • Density Functional Theory
  • Fluorine / chemistry*
  • Models, Molecular
  • Models, Theoretical
  • Molecular Conformation
  • Molecular Structure
  • Nickel / chemistry*
  • Oxidation-Reduction
  • Phosphines / chemistry*

Substances

  • Coordination Complexes
  • Phosphines
  • Fluorine
  • Nickel
  • phosphine