| Project/Area Number |
16K05687
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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 | Ochanomizu University |
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Principal Investigator |
Yajima Tomoko お茶の水女子大学, 基幹研究院, 准教授 (10302994)
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Project Status |
Completed (Fiscal Year 2018)
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| Budget Amount *help |
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2018: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | 可視光反応 / 有機色素 / ペルフルオロアルキル / レドックス触媒 / ラジカル反応 / 含フッ素化合物 / 合成化学 / 有機触媒 |
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| Outline of Final Research Achievements |
Fluorine-containing compounds have unique properties resulting from the high electronegativity and small size of the fluorine atom and the strong nature of the F bond. Perfluoroalkylated compounds are one of the most essential compounds not only as pharmaceuticals but also as functional materials, and the development of efficient synthetic methods is essential.
Under such circumstanses, we have developed some metal-free, visible-light-induced perfluoroalkylation of various aokenes and alkynes. This process uses eosin Y, which is inexpensive, as a photoredox catalyst, and the method is operationally easy. This strategy allows convenient access to various perfluoroalkylated compounds, because easily available perfluoroalkyl halides are used as the F source. This green method is highly functional-group-tolerant and can provides a new efficient route to fluoroalkylated compounds.
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| Academic Significance and Societal Importance of the Research Achievements |
可視光レドックス反応は、用いるエネルギーが小さく太陽光でも進行するため、環境適用型の反応として注目されている。中でも本反応は希少金属を用いず、安価で入手容易な有機色素を触媒とするため、環境にやさしく、TMSCF3（プラカッシュ試薬）、梅本試薬、Togni試薬などの高価なフッ素源でなく、それらの原料でもある、入手容易なハロゲン化ペルフルオロアルキルをラジカル前駆体として用いるため、トリフルオロメチル以外のペルフルオロアルキルも導入可能であり、様々な含フッ素化合物を合成することのできる優れた反応である。また、有機色素を用いた可視光反応の反応機構の解明は、今後の合成分野に貢献できると考えられる。
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