Electrophilic substitution reactions using an electrogenerated ArS(ArSSAr) + cation pool as an ArS + equivalent

Kouichi Matsumoto, Yuki Kozuki, Yosuke Ashikari, Seiji Suga, Shigenori Kashimura, Jun Ichi Yoshida

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24 Citations (Scopus)

Abstract

Arylbis(arylthio)sulfonium ions (ArS(ArSSAr) +), which were generated and accumulated by the low-temperature electrolysis of diaryl disulfide (ArSSAr), were found to serve as ArS + equivalent in electrophilic substitution reactions of aromatic compounds, enolizable ketones, enol acetates, ketene silyl acetals and allylsilanes to give the corresponding arylthiolated products.

Original languageEnglish
Pages (from-to)1916-1919
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number15
DOIs
Publication statusPublished - Apr 11 2012

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Keywords

  • Disulfide
  • Electrochemistry
  • Electrophilic substitution
  • Oxidation
  • Sulfenium ion

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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