Organic synthesis using carbocations generated by electron transfer reactions

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Abstract

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.

Original languageEnglish
Pages (from-to)1010-1020
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume64
Issue number10
DOIs
Publication statusPublished - Oct 2006
Externally publishedYes

Keywords

  • Carbocation
  • Cation flow method
  • Cation pool method
  • Combinatorial synthesis
  • Electrochemical oxidation
  • Electron transfer reaction
  • Microreactor

ASJC Scopus subject areas

  • Organic Chemistry

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