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2020 Fiscal Year Final Research Report

Innovative Methodologies for Carbon-Fluorine Bond Activation

Research Project

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Project/Area Number 18K05116
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionUniversity of Tsukuba

Principal Investigator

FUJITA Takeshi  筑波大学, 数理物質系, 助教 (60603066)

Project Period (FY) 2018-04-01 – 2021-03-31
Keywords有機合成化学 / フッ素 / 触媒
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.

Free Research Field

有機合成化学

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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Published: 2022-01-27  

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