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Synthesis 2011(1): 33-44  
DOI: 10.1055/s-0030-1258330
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Introduction of a Tetrafluoroethylene (-CF2CF2-) Unit into Organic Molecules

Tsutomu Konno*, Shinya Takano, Yoshikazu Takahashi, Hideaki Konishi, Yusuke Tanaka, Takashi Ishihara
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan
Fax: +81(75)7247580; e-Mail: konno@chem.kit.ac.jp;
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Publikationsverlauf

Received 7 September 2010
Publikationsdatum:
15. November 2010 (online)

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Abstract

The reductive coupling of 4-bromo-3,3,4,4-tetrafluorobut-1-ene with 2.4 equivalents of various carbonyl compounds proceeded very smoothly in the presence of 2.4 equivalents of MeLi/LiBr-free at -78 ˚C for two hours, giving the corresponding adducts in high to excellent yields. On the other hand, triethyl(1,1,2,2-tetrafluorobut-3-enyl)silane, which could be prepared by treatment of 4-bromo-3,3,4,4-tetrafluorobut-1-ene and chlorotriethylsilane with magnesium at 0 ˚C for three hours, reacted with some aldehydes in the presence of 1 mol% of tetrabutylammonium fluoride, the desired adducts being obtained in good to high yields.

Key words

tetrafluoroethylene - MeLi/LiBr-free - triethyl(1,1,2,2-tetrafluorobut-3-enyl)silane - reductive coupling

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Unpublished results.