マグネシウム金属還元法の新たな炭素-炭素結合および炭素-ケイ素結合形成への応用  [in Japanese] Novel Development of Carbon-Carbon Bond and Carbon-Silicon Bond Formation by Magnesium-promoted Reduction  [in Japanese]

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Author(s)

    • 前川 博史 Maekawa Hirofumi
    • 長岡技術科学大学技学研究院物質材料工学専攻 Department of Materials Science and Technology, Graduate School of Engineering, Nagaoka University of Technology

Abstract

<p>Magnesium is one of the most familiar elements. However, magnesium may only remind organic chemists of Grignard reaction. Some chemists will add pinacol coupling and what type of reactions will you say in relation with magnesium? Magnesium has many benefits such as eco-friendly, reactive, stored in the air, cheap, etc. We used this material as an electron transfer reagent for organic reactions and reported reductive coupling reactions with new combination of reagents. Electron-deficient carbons such as carbonyl carbons and the β-carbon of conjugated carbonyl compounds reacted with electrophiles to form carbon-carbon bonds and carbon-silicon bonds through umpolung by magnesium-promoted reduction. In this article, new development of magnesium-promoted coupling reactions will be reported in detail, especially, application of silylation to non-benzenoid aromatic compounds, synthesis of multi-functionalized allenes, reductive carboxylation, novel synthesis of fluorine-containing compounds by trifluoroacetylation, abnormal introduction of a trifluoroacetyl group to aromatic rings, and silylation and trifluoroacetylation of vinylpyridines.</p>

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 75(3), 240-252, 2017

    The Society of Synthetic Organic Chemistry, Japan

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