2021 Fiscal Year Final Research Report
Development of boron-catalyzed direct amidation reactions in aqueous solution
| Project/Area Number |
19K06994
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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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| Review Section |
Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
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| Research Institution | Matsuyama University (2020-2021)
Kanazawa University (2019) |
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Principal Investigator |
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| Project Period (FY) |
2019-04-01 – 2022-03-31
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| Keywords | 直接的アミド化 / ホウ素触媒 |
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| Outline of Final Research Achievements |
In this study, we investigated the development of boronic acid catalysts that can give amides from various carboxylic acids and amines at room temperature for several hours without racemization, and that can be catalyzed in aqueous solution. Since dinuclear boron complexes were expected to be important intermediates in catalytic amidation reactions, we investigated dinuclear boron complexes bridging two boronic acid moieties. Unfortunately, we were unable to develop a catalyst that would facilitate the desired amidation reaction in aqueous solution because our research time was limited by coronavirus infection. However, although somewhat divergent from the original purpose of the study, valuable insights were gained from the development of amidation reactions in aqueous and alcohol solvents.
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| Free Research Field |
有機化学
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| Academic Significance and Societal Importance of the Research Achievements |
二核ホウ素錯体について，ふたつのボロン酸部位を有することから，その極性が高くなって有機溶媒への溶解性が減少し，また，ふたつのボロン酸部位から脱水反応が容易に進行して複数の化合物を与えることから，合成には更なる合成研究が必要であることが示唆された．また，水もしくはアルコール溶媒中で，カルボン酸を活性化した中間体の反応性について広く研究を行った結果，僅かな電子的および立体的要因により，加溶媒分解の様子が変わることが分かった．ボロン酸触媒においても，活性中間体を経ることが予想され，加水分解や加アルコール分解を抑制するために触媒分子における電子的および立体的要因の考察が必須であるという知見が得られた．
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