2018 Fiscal Year Final Research Report
Merging Theoretical and Experimental Chemistry towards Introduction of Fluorinated Functional Groups
| Project/Area Number |
16H06214
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| Research Category |
Grant-in-Aid for Young Scientists (A)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | The University of Tokyo |
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Principal Investigator |
Hirano Keiichi 東京大学, 大学院薬学系研究科(薬学部), 助教 (40633392)
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Keywords | フッ素 / 芳香族メタル化 / 銅 / 銀 |
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| Outline of Final Research Achievements |
Efficient chemical processes for introduction of fluorine-containing functional groups are of highly importance since fluorine is widely found among pharmaceuticals and functional materials. We have conducted a research dealing with aromatic perfluoroalkylation on the basis of deprotonative matalation of arenes with transition metal-based amide ate bases. Arylcopper species generated by deprotonative metalation were found to be perfluoroalkylated in combination with perfluoroalkyliodanes. In addition, we also worked on development of novel deprotonative metalation methodology in order to improve the process above. A silver ate base was newly designed and found to be highly reactive and chemoselective in deprotonative metalation reaction.
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| Free Research Field |
有機化学
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| Academic Significance and Societal Importance of the Research Achievements |
申請者ら独自のアミド型銅アート塩基を用いた芳香環のメタル化反応を基盤として多種多様な（ヘテロ）芳香環に嵩高い RF 基を導入する手法の確立に取り組み一定の成果を得たが、高収率で目的物を得るには至らなかった。そこで全く新しいメタル化反応として、芳香環の直接的銀化反応を開発し、生じるアリール銀を用いる方針を立てた。申請者らが設計した TMP2Ag(CN)Li2 は複雑に官能基化された芳香環でも速やかに銀化できることを見出した。 アリール銀の発生法ならびに反応性の化学はまだまだ未開拓であるが、本成果により簡便にアリール銀が発生できるようになったので、これを契機に研究が活発化すると考えられる。
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