Development of novel synthetic methods controlled by the reduction potential of substrates and the reactivity of leaving groups in the reaction media
| Project/Area Number |
16K05768
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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 | Nagaoka University of Technology |
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Principal Investigator |
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| Co-Investigator(Kenkyū-buntansha) |
山本 祥正 東京工業高等専門学校, 機械工学科, 准教授 (90444190)
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Project Status |
Completed (Fiscal Year 2018)
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| Budget Amount *help |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2018: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
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| Keywords | マグネシウム / 電子移動 / 還元 / 環境調和 / 有機合成 / カップリング / 脱離基 / 合成化学 / 元素戦略 / 環境調和型反応 |
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| Outline of Final Research Achievements |
In this research, magnesium was used as a reducing agent in synthetic organic reactions, which was commercially available and cheap. Aromatic compounds with a leaving group on a vinyl carbon atom were prepared and substitution reactions of the leaving group were investigated under the conditions of Mg-promoted reduction. As a result, the leaving group was replaced with a silyl group when a cinnamic acid ester with a leaving group at beta-position of the carbonyl group was reduced in THF. The silylated compound was further reduced in NMP in the presence of another nucleophile to give a variety of compounds with two functional groups at the benzylic position. Reduction of aliphatic conjugated esters and styrenes with a leaving group also gave substitution compounds under the similar reaction conditions.
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| Academic Significance and Societal Importance of the Research Achievements |
有機合成反応は，日常生活に使われる様々な有機物質や有機材料，さらにはそれらの中間体を合成する重要な手法である。歴史は古く，これまでに無数の反応が開発されているが，バイオマスなどの石油代替資源を有効に活用して今後も安価に自由自在に有機物質を合成するには，さらなる有機物質構造変換法の開発が必要である。遷移金属錯体を用いる有機合成と比べて電子移動を用いた有機合成反応分野は研究者数が少ないが，相補的に幅広く有機合成分野を網羅する上で不可欠な技術分野である。また本研究で還元剤として用いたマグネシウムは地球上に広く分布し，入手容易であるため，その有機合成への活用は我が国の元素戦略上も有益である。
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Report
(4 results)
Research Products
(24 results)
