Organic Synthesis Using Carbocations Generated by Electron Transfer Reactions

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  • Suga Seiji
    Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University

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  • 電子移動反応による炭素カチオンの創製を機軸とする新しい有機合成
  • デンシ イドウ ハンノウ ニ ヨル タンソ カチオン ノ ソウセイ オ キジク ト スル アタラシイ ユウキ ゴウセイ

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We have developed the “cation pool” method in which carbocations such as alkoxycarbenium ions and N-acyliminium ions are generated and accumulated in conventional reaction media by low temperature electrochemical oxidation. The carbocations thus produced are allowed to react with a variety of nucleophiles. Various organic transformations using the cation pool method, such as reductive radical couplings, cationic carbohydroxylations, three-component couplings, and additions of organic radicals, have also been developed. Combinatorial sequential synthesis using the “cation flow” method, in which carbocations are generated in an electrochemical microflow system, has been achieved as well.

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