Challenge to Enantioselective C-F Bond Activation
| Project/Area Number |
24655073
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Synthetic chemistry
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| Research Institution | Gunma University |
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Principal Investigator |
AMII Hideki 群馬大学, 大学院理工学府, 教授 (00284084)
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| Project Period (FY) |
2012-04-01 – 2015-03-31
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| Project Status |
Completed (Fiscal Year 2014)
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| Budget Amount *help |
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2012: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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| Keywords | 有機合成化学 / フッ素 / 不活性結合 / 不斉反応 / 脱フッ素化 / クロスカップリング / 選択的変換 / 結合活性化 |
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| Outline of Final Research Achievements |
Organofluorine compounds are widely used as materials such as polymer, liquid crystals, pharmaceutical and agrochemical compounds, and so on. Meanwhile, a new technology for highly selective synthesis of enantiomerically pure organofluorine compounds has been required. Toward stereoselective C-F bond activation, we examined Lewis acid-mediated defluorinative alkylation using gem-difluoromethylene compounds. Organoaluminum compounds were found to promote C-F bond activation of β-fluoro ethanol derivativess. When β, β-difluoro ethanols were treated with a stoichiometric amount of trimethylaluminum, defluorination and the subsequent methylation proceeded smoothly to give the ketones in moderate yields. For the preparation of several gem-difluoromethylene substrates, we developed the cross-coupling routes to 2-aryl-2,2-difluoroacetates. Furthermore, a new strategy for the synthesis of monofluoro compounds involving Mg-promoted defluorination of 2-aryldifluoroacetates have been invented.
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Report
(4 results)
Research Products
(10 results)
