2019 Fiscal Year Final Research Report
Development of new synthetic methods by the C-F bond activation
| Project/Area Number |
17K05794
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Nihon University |
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Principal Investigator |
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| Project Period (FY) |
2017-04-01 – 2020-03-31
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| Keywords | フッ素 / パラジウム / トリフルオロメチル基 / 炭素ーフッ素結合活性化 / ジフルオロメチル基 |
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| Outline of Final Research Achievements |
I examined the Pd-catalyzed reactions of two types of fluorine-containing allylic esters with nucleophiles, and succeeded in achieving new type of reactions. For example, the reaction of 2-fluoroallylic esters with several types of nucleophiles provided three components coupling product in high regioselectivity. Furthermore, I demonstrated the reactions of 2,3,3-trifluoroallylic esters with several types of nucleophiles and succeeded in obtaining the trifluoromethyl group containing coupling products, which was proceeded through the C-2 attack of nucleophiles to allylic component and fluorine atom shift from C-2 position to C-3 position. I also examine the reaction of 2,3,3-trifluoroallylic esters with hydride, and succeeded in constructing difluoromethyl group in regioselectively.
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| Free Research Field |
有機合成
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| Academic Significance and Societal Importance of the Research Achievements |
医農薬品や機能材料として有用な含フッ素有機化合物の更なる効率的な変換手法の確立を目指した研究を行い，これまでに例の無いパラジウム触媒反応を実現した．例えば，強固な結合である炭素ーフッ素結合の開裂を伴いつつ求核剤となる有機分子２つを一挙の導入する反応や，含フッ素有機化合物に求核剤を導入しつつ分子内でフッ素原子を移動させつつトリフルオロメチル基を構築するタイプの反応の実現に成功した．更には，末端のジフルオロオレフィンに対して位置選択的なヒドリド還元を進行させてジフルオロメチル基を構築する反応の開発にも成功した．
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