Journal of Fluorine Chemistry p. 29 - 37 (2015)
Update date:2022-08-16
Topics:
Ichitsuka, Tomohiro
Takanohashi, Tsuyoshi
Fujita, Takeshi
Ichikawa, Junji
A thermally stable 2,2-difluorovinylzinc-TMEDA complex was prepared via a deprotonation-transmetallation sequence starting from commercially available 1,1-difluoroethylene. The complex thus formed was successfully applied to transition metal-catalyzed cross-coupling reactions with a wide range of organic halides, which led to the syntheses of 2,2-difluorovinyl compounds. On treatment with the difluorovinylzinc-TMEDA complex in the presence of an appropriate palladium or copper catalyst, alkenyl, alkynyl, allyl, and benzyl halides effectively underwent difluorovinylation to afford 1,1-difluoro-1,3-dienes, 1,1-difluoro-1,3-enynes, 1,1-difluoro-1,4-dienes, and (3,3-difluoroallyl)arenes, respectively.
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