Preparation of perfluoro compounds through the regioselective cleavage of a carbon-fluorine bond
| Project/Area Number |
25708018
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| Research Category |
Grant-in-Aid for Young Scientists (A)
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| Allocation Type | Partial Multi-year Fund |
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| Research Field |
Synthetic chemistry
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| Research Institution | Osaka University |
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Principal Investigator |
Ohashi Masato 大阪大学, 工学(系)研究科(研究院), 准教授 (60397635)
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| Project Period (FY) |
2013-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥26,390,000 (Direct Cost: ¥20,300,000、Indirect Cost: ¥6,090,000)
Fiscal Year 2016: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2015: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2014: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2013: ¥15,080,000 (Direct Cost: ¥11,600,000、Indirect Cost: ¥3,480,000)
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| Keywords | 炭素フッ素結合活性化 / 分子変換反応 / パーフルオロ化合物 / パラジウム / ニッケル / 銅 |
|---|
| Outline of Final Research Achievements |
The Pd(0)-mediated regioselective C-F bond cleavage of perfluoroalkene has been developed by adopting the proper choice of the Lewis acid additive. Thus, the addition of tris(pentafluorophenyl)borane to eta2-hexafluoro propylene Pd(0) complex allowed the sp3-C-F bond cleavage in a selective manner to yield a cationic perfluoroallyl complex. In contrast, the use of BF3-etherate resulted in the quantitative sp2-C-F bond cleavage to yield a perfluoropropenyl complex.
We found that the allylic C-F bond cleavage would be the kinetically dominant process in our system, and that both steric hindrance and nucleophilicity of the counter anion or the resultant conjugated base would be the key to determine the structure of C－F bond cleavage product.
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Report
(5 results)
Research Products
(245 results)
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[Journal Article] Ni-Catalyzed [4+3+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Dienynes: Scope and Mechanistic Insights2013
Author(s)
R. Yamasaki, M. Ohashi, K. Maeda, T. Kitamura, M. Nakagawa, K. Kato, T. Fujita, R. Kamura, K. Kinoshita, H. Masu, I. Azumaya, S. Ogoshi, S. Saito
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Journal Title
Chemistry - A European Journal
Volume: 19
Issue: 10
Pages: 3415-3425
DOI
Related Report
Peer Reviewed
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