2021 Fiscal Year Final Research Report
Development of Practical Catalytic Trifluoromethylation Reaction
| Project/Area Number |
19K15572
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| Research Category |
Grant-in-Aid for Early-Career Scientists
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| Allocation Type | Multi-year Fund |
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| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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| Research Institution | Kwansei Gakuin University |
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Principal Investigator |
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| Project Period (FY) |
2019-04-01 – 2022-03-31
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| Keywords | 1 電子移動 / トリフルオロメチル化 / 不活性結合活性化 / EDA 錯体 / 電子触媒クロスカップリング反応 |
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| Outline of Final Research Achievements |
To use trifluoromethoxybenzenes (CF3OAr) as trifluoromethylating agents, activation of the compounds by Lewis acids, light or electricity was studied. The O-CF3 bond of CF3OAr was not cleaved by any methods, however, methylation of amines with anisole through activation of the O-CH3 bond by Lewis acids was achieved. Formation of an electron donor-acceptor complex between an organometallic compound and a CF3OAr was suggested. CF3O group was found to work as a leaving group in the electron-catalyzed cross-coupling reaction.
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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 |
本研究で，O-CF3 結合が，O-CH3 結合に比べて，酸・光・還元条件下で圧倒的に安定であることが判った．ArOCH3 では O-CH3 結合が切れるのでメチル化反応への利用，ArOCF3 では Ar-O 結合が切れるのでアリール化反応への利用が期待できる．実際に，芳香環上の CF3O 基が脱離する電子触媒クロスカップリング反応が進行することが判ったが，ここでは，医薬品や機能性分子に含まれる重要な骨格としてのビアリールを構築できるためこの反応を効率化することの意義は大きく，そのきっかけを作った本研究の価値は高い．
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