2,2,3,3-Tetrafluoronickelacyclopentanes Generated via the Oxidative Cyclization of Tetrafluoroethylene and Simple Alkenes: A Key Intermediate in Nickel-Catalyzed C–C Bond-Forming Reactions

DOI Web Site Research Data 14 Citations 79 References
  • Masato Ohashi
    Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
  • Takuya Kawashima
    Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
  • Tomoaki Taniguchi
    Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
  • Kotaro Kikushima
    Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
  • Sensuke Ogoshi
    Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan

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Description

Oxidative cyclization of tetrafluoroethylene (TFE) and ethylene with Ni(0) resulted in the formation of a five-membered nickelacycle. In the presence of PPh3 as an auxiliary ligand, the partially fluorinated five-membered nickelacycle was isolated and the structure was determined by X-ray analysis. This nickelacycle was found not only to react stoichiometrically with enones to give a cross-trimerization product but also to be a key reaction intermediate in the Ni(0)-catalyzed cotrimerization of TFE and ethylene, leading to 5,5,6,6-tetrafluoro-1-hexene.

Journal

  • Organometallics

    Organometallics 34 (9), 1604-1607, 2015-04-30

    American Chemical Society (ACS)

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