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Updated: Jan 20, 2026
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Fluorine-Substituted Arylphosphine for an NHC-Ni(I) System, Air-Stable in a Solid State but Catalytically Active in
Kouki Matsubara1, Takahiro Fujii2, Rion Hosokawa3
1Department of Chemistry, Fukuoka University, 8-19-1 Nanakuma, Fukuoka 814-0180, Japan. kmatsuba@fukuoka-u.ac.jp.
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.
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