Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 170, Issue -, Pages 29-37Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2014.12.003
Keywords
Difluoroalkene; Organozinc; Cross-coupling reaction; Palladium; Copper; Catalyst
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Funding
- JSPS KAKENHI [25288016]
- Asahi Glass Foundation
- Grants-in-Aid for Scientific Research [26870079, 25288016] Funding Source: KAKEN
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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. (C) 2014 Elsevier B.V. All rights reserved.
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