2022 Fiscal Year Final Research Report
Development of general synthetic method for tetraarylammonium salts
| Project/Area Number |
21K18955
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| Research Category |
Grant-in-Aid for Challenging Research (Exploratory)
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| Allocation Type | Multi-year Fund |
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| Review Section |
Medium-sized Section 33:Organic chemistry and related fields
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| Research Institution | Nagoya University |
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Principal Investigator |
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| Project Period (FY) |
2021-07-09 – 2023-03-31
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| Keywords | アンモニウム塩 / C-N結合形成 / フォトレドックス触媒 / テトラアリールアンモニウム塩 |
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| Outline of Final Research Achievements |
In this study, in order to establish a method for synthesizing tetraarylammonium salts, we investigated three different synthetic pathways including characteristic intermediates. These approaches include (1) azasilatriptycene and azaphosphatriptycene, (2) o-bromophenylsilyl-substituted triarylamines, and (3) azaboranthracene. In the synthetic pathway (2), the reaction of the key intermediate, o-bromophenylsilyl-substituted triarylamine, with Pd(0) complex gave a product in which the resulting C-Pd bond and the pyramidalized nitrogen atom of the triarylamine are close to each other. However, the C-N bond reductive elimination reaction from this product could not be observed. We believe that it may be possible to obtain the desired product by induction of the C-N reductive elimination by using further transmetallation or oxidation.
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| Free Research Field |
有機金属化学・有機合成化学
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| Academic Significance and Societal Importance of the Research Achievements |
本研究では主に3種類の合成経路を用いてテトラアリールアンモニウム塩の一般的合成法の開発を目指した。目的の手法開拓には至らなかったものの、以下2点について学術的に興味深い現象を見いだした。(1) 置換基の種類によりトリフェニルアミン誘導体の窒素原子がピラミッド化すること、すなわち通常は塩基性のほとんど無いトリフェニルアミンの窒素原子に塩基性を付与できることを示した。(2) アザホスファトリプチセンの窒素とリンがいずれも金属に配位して、直線型の配位高分子を形成すること、すなわちトリプチセンの軸方向における配位化学を展開可能であることを示した。
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