2018 Fiscal Year Final Research Report
Development of catalytic aerial oxidation using oranocatalyst
| Project/Area Number |
16K05764
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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 |
Synthetic chemistry
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| Research Institution | Iwate University |
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Principal Investigator |
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| Research Collaborator |
OKAZAKI masaaki
SEINO hidetake
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Keywords | パーフルオロシクロペンテン / カップリング反応 / ラジカル活性種 / 空気酸化 |
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| Outline of Final Research Achievements |
In 2015, we reported that the oxidative homocoupling reaction of Grignard reagents could be performed by using heptafluorotolyl-substituted perfluorocyclopentene in the presence of atmospheric oxygen molecules. In this study, we clarified the active catalytic species to be heptafluorotolyl- substituted perfluorocyclopentadienyl radical. The radical species could be also used for the oxidative homocoupling reaction of Grignard reagents. The turnover number (TON) was over 30 for the coupling reactions of PhMgBr to give biphenyl. The organocatalyst could couple thienylmagnesium compounds to give bithiophene derivatives in up to 94% yield. Furthermore, the reaction could be utilized for the synthesis of the synthetic intermediate of biphosphine ligand.
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| Free Research Field |
有機合成化学
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| Academic Significance and Societal Importance of the Research Achievements |
開発したヘプタフルオロトリル基を有するパーフルオロシクロペンテン誘導体は、2017年に東京化成（株）より売り出しが開始された。これにより多くの研究者に利用可能となった。またその触媒活性種を前述のパーフルオロシクロペンテン誘導体から簡単に別途合成する事ができるようになったため、今後空気を利用する酸化反応に対して応用化が期待できる。
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