Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry

Shunsuke Fujie, Kouichi Matsumoto, Seiji Suga, Toshiki Nokami, Jun ichi Yoshida

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

ArS(ArSSAr)+ (arylbis(arylthio)sulfonium ions), which were generated and accumulated by the electrochemical oxidation of diaryl disulfides (ArSSAr) in CH2Cl2 at -78 °C, reacted with alkenes to give the corresponding diarylthio-substituted compounds in a stereospecific manner in good yields, when the reaction was quenched with a soft nucleophile, such as allylsilanes, ketene silyl acetals, and triethylamine. A mechanism involving the initial formation of an episulfonium ion followed by ring-opening by the attack of ArSSAr has been suggested. The reactions of ArS(ArSSAr)+ with alkynes also took place to give 1,2-diorganothio-substitued alkenes stereoselectively under similar conditions.

Original languageEnglish
Pages (from-to)2823-2829
Number of pages7
JournalTetrahedron
Volume66
Issue number15
DOIs
Publication statusPublished - Apr 10 2010
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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