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      Pentamethylcyclopentadienyl rhodium(III) trifluorovinyl phosphine complexes and attempted intramolecular dehydrofluorinative coupling of pentamethylcyclopentadienyl and trifluorovinyl phosphine ligands

      Barnes, Nicholas; Brisdon, Alan K.; Nieuwenhuyzen, Mark; Pritchard, Robin G.; Saunders, Graham C.
      DOI
       10.1016/j.jfluchem.2007.04.003
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      Barnes, N., Brisdon, A.K., Nieuwenhuyzen, M., Pritchard, R.G. & Saunders, G.C. (2007). Pentamethylcyclopentadienyl rhodium(III) trifluorovinyl phosphine complexes and attempted intramolecular dehydrofluorinative coupling of pentamethylcyclopentadienyl and trifluorovinyl phosphine ligands. Journal of Fluorine Chemistry, 128(8), 943-951.
      Permanent Research Commons link: https://hdl.handle.net/10289/3923
      Abstract
      The trifluorovinyl phosphine complexes [Cp*RhCl₂{PR3−x(CF CF₂)x}] (1 x = 1, a R = Ph, b Pri, c Et; 2 x = 2, R = Ph) have been prepared by treatment of [Cp*RhCl(μ-Cl)]₂ with the relevant phosphine. The salt [Cp*RhCl(CNBut){PPh₂(CF CF₂)}]BF₄, 3, was prepared by addition of ButNC to 1a in the presence of NaBF₄. The salt [Cp*RhCl{κP,κS-(CF₂ CF)PPh(C₆H₄SMe-2)}]BF₄ was prepared as a mixture of cis (5a) and trans (5b) isomers by treatment of [Cp*RhCl(μ-Cl)]₂ with the phosphine-thioether (CF₂ CF)PPh(C₆H₄SMe-2), 4, in the presence of NaBF₄. The structures of 1a–c and 5a have been determined by single-crystal X-ray diffraction. Intramolecular dehydrofluorinative carbon–carbon coupling between pentamethylcyclopentadienyl and trifluorovinylphosphine ligands of 1a, 3 and 5 has been attempted. No reaction was observed on treatment of the neutral complex [Cp*RhCl₂{PPh₂(CF CF₂)}], 1a, with proton sponge, however, 5a underwent dehydrofluorinative coupling to yield [{η⁵,κP,κS-(C₅Me₄CH₂CF CF)PPh(C₆H₄SMe-2)}RhCl]BF₄, 6. Other reactions, in particular addition of HF across the vinyl bonds of 5, occurred leading to a mixture of products. The cation of 3 underwent similar reactions.
      Date
      2007
      Type
      Journal Article
      Publisher
      Elsevier
      Collections
      • Science and Engineering Papers [3124]
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