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. 2015 May 27;137(20):6496-9.
doi: 10.1021/jacs.5b03587. Epub 2015 May 14.

Nickel-Catalyzed Formation of Fluorine-Containing Ketones via the Selective Cross-Trimerization Reaction of Tetrafluoroethylene, Ethylene, and Aldehydes

Masato Ohashi  1 , Hiroshi Shirataki  1 , Kotaro Kikushima  1 , Sensuke Ogoshi  1   2
Affiliations

Nickel-Catalyzed Formation of Fluorine-Containing Ketones via the Selective Cross-Trimerization Reaction of Tetrafluoroethylene, Ethylene, and Aldehydes

Masato Ohashi et al. J Am Chem Soc. .

Abstract

In the presence of a catalytic amount of Ni(cod)2 and IPr (1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), a cross-trimerization reaction of tetrafluoroethylene (TFE), ethylene, and aldehydes proceeded in a selective manner to afford a variety of 4,4,5,5-tetrafluoro-1-pentanone derivatives in good to excellent yields. The present system involves a five-membered nickelacycle key intermediate generated via the oxidative cyclization of TFE and ethylene.

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