Development of Asymmetric Photofluorination
| Project/Area Number |
18K06585
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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 47010:Pharmaceutical chemistry and drug development sciences-related
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| Research Institution | University of Shizuoka |
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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 | 不斉合成 / フッ素 / 相間移動触媒 / C-H結合 / ラジカル / ケトン / C-H変換 / 光 / フォトエノール / フッ素化 / 不斉反応 / 触媒 |
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| Outline of Final Research Achievements |
The C-H fluorination of a benzophenone derivative, which has ketone unit enable to be excited by photo-irradiation, provided not mono-fluorination product but di-fluorination product. On the other hand, mono-fluorination product was selectively obtained by using HAT catalyst. However, the photo-induced C-H fluorination did not proceed under phase-transfer catalyst conditions in non-polar solvents. We also tried to confirm the possibility of asymmetric induction between the radical intermediate and chiral fluorinating reagent, which is generated from the chiral phase-transfer catalyst with Selectfluor. As a result of some examinations, it was found that the chirality was induced in the radical fluorination.
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| Academic Significance and Societal Importance of the Research Achievements |
新しいフッ素化合物を供給する方法論の開発は、生命科学研究において重要な課題であるが、最も効率的と考えられるC-H結合のフッ素化に関して、その立体制御を成す一般的な方法論は未だ確立されていない。そのため、C-Hフッ素化反応の立体制御法の開発を目指した本研究は学術的に挑戦的である。一方、その生成物は含フッ素ケミカルスペースの拡充に貢献することから、意義ある課題である。今回、ラジカル中間体をキラル相間移動触媒から調製されるキラルフッ素化剤と反応させることで、その立体制御が可能であることを示すことができた。これによりラジカル的なフッ素導入における立体制御の新たな方法論を提供するきっかけを得た。
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Report
(4 results)
Research Products
(42 results)
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[Journal Article] 18F-Labeled dihydromethidine: Positron emission tomography radiotracer for imaging of reactive oxygen species in intact brain2020
Author(s)
Hiromichi Egami, Satoshi Nakagawa, Yuki Katsura, Masakatsu Kanazawa, Shingo Nishiyama, Toshihiro Sakai, Yasushi Arano, Hideo Tsukada, Osamu Inoue, Kenichiro Todoroki, Yoshitaka Hamashima
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Journal Title
Org. Biomol. Chem.
Volume: 18
Issue: 13
Pages: 2387-2391
DOI
Related Report
Peer Reviewed
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