Innovative Methodologies for Carbon-Fluorine Bond Activation
| Project/Area Number |
18K05116
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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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| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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| Research Institution | University of Tsukuba |
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Principal Investigator |
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| Project Period (FY) |
2018-04-01 – 2021-03-31
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| Project Status |
Completed (Fiscal Year 2020)
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| Budget Amount *help |
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | 有機合成化学 / フッ素 / 触媒 |
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| Outline of Final Research Achievements |
Because carbon-fluorine bonds are stable bonds, it has been difficult to carry out chemical transformations while cleaving them. In contrast, focusing on fluorine elimination using metals and HF elimination using acids, I developed a C-F bond activation method under mild reaction conditions.
By using fluoroalkenes as substrates, metal-mediated β-fluorine elimination was combined with oxidative cyclization, nucleophilic addition, or metalacyclopropanation to produce high-value-added fluorine-containing heterocyclic compounds.
Furthermore, an intremorecular C-F/C-H coupling was achieved by HF elimination followed by electrophilic addition on treatment of fluoroarenes with arenes in the presence of an appropriate acid.
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| Academic Significance and Societal Importance of the Research Achievements |
炭素-フッ素結合は安定な結合であるため、これを切断するには加熱などの過酷な条件が必要であった。これに対して本研究課題では、金属を用いるβ-フッ素脱離や酸を用いるHF脱離を鍵とする種々のC-F結合活性化法を開発してきた。これらの反応はいずれも、穏和な反応条件下でC-F結合を切断するだけでなく、複雑な骨格を持つ含フッ素化合物の構築法となった。このことは、学術的に意義深い革新的なC-F結合活性化法を提供できたと考えている。また、複数のフッ素を持つ基質の選択的なC-F結合活性化により、医農薬や材料として有望な含フッ素化合物を効率的に合成できたため、今後の応用研究にこれらを供給できる。
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Report
(4 results)
Research Products
(40 results)
