| 研究課題/領域番号 |
16J11354
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| 研究機関 | 京都大学 |
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研究代表者 |
Zhao Qiang 京都大学, 工学研究科, 特別研究員(DC1)
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| 研究期間 (年度) |
2016-04-22 – 2019-03-31
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| キーワード | carbene / triazole / acceptor/acceptor / arene compounds / enaminones |
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| 研究実績の概要 |
we have designed and synthesized a new kind of triazole which possessing a unique reactivity with simple unactivated arene compounds. The new developed model triazole is named “4-acyl-1-mesyl-1,2,3-triazole”. We found that it could be generated acceptor/acceptor rhodium carbene complex in the presence of rhodium catalyst. The generated acceptor/acceptor rhodium carbene complex could react with unactivated simple arene compounds, leading to the formation of enaminones. Interestingly, the reaction takes place exclusively with the aromatic C(sp2)-H bonds in the presence of benzylic C(sp3)-H bonds. We also did some experiments to probe the reaction mechanisms. An electrophilic aromatic substitution pathway via a zwitterionic intermediate might be the real reaction mechanism.
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| 現在までの達成度 (区分) |
現在までの達成度 (区分)
2: おおむね順調に進展している
理由
We have sucessfully synthesized a new kind of triazole named “4-acyl-1-mesyl-1,2,3-triazole” which could be used as acceptor/acceptor carbene precursor. We found this new synthesized triazole could be generated acceptor/acceptor rhodium carbene complex in the presence of rhodium catalyst. The generated acceptor/acceptor rhodium carbene complex could react with unactivated simple arene compounds, leading to the formation of enaminones. Interestingly, the reaction takes place exclusively with the aromatic C(sp2)-H bonds in the presence of benzylic C(sp3)-H bonds.
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| 今後の研究の推進方策 |
In the following year, we are going to study the intramolecular reactions using acceptor/acceptor carbene precursors. we also want to develop new reactions using the strategy of in-situ generation of acceptor/acceptor carbene complex from 4-acyl-1-sulfonyl-1,2,3-triazoles. We hope we can develop unique new reactions using our new developed strategy which can’t be reached by using traditional donor/acceptor carbenes generated from triazoles.
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