The Addition of ArSSAr to Alkenes: The Implications of a Cationic Chain Mechanism Initiated by Electrogenerated ArS(ArSSAr)+

Kouichi Matsumoto, Tomonari Sanada, Hayato Shimazaki, Kazuaki Shimada, Shino Hagiwara, Shunsuke Fujie, Yosuke Ashikari, Seiji Suga, Shigenori Kashimura, Jun ichi Yoshida

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24 Citations (Scopus)

Abstract

The addition reactions of diaryl disulfides (ArSSAr) to alkenes and alkynes were achieved with a catalytic amount of an arylbis(arylthio)sulfonium ion (ArS(ArSSAr)+), which was generated and accumulated by low-temperature electrolysis of ArSSAr, to give the corresponding diarylthiolated products. The electrolysis of a mixture of ArSSAr and an alkene with a catalytic amount of electricity was also effective to drive the reactions. A cation chain mechanism mediated by ArS(ArSSAr)+ as a chain carrier is suggested.

Original languageEnglish
Pages (from-to)325-329
Number of pages5
JournalAsian Journal of Organic Chemistry
Volume2
Issue number4
DOIs
Publication statusPublished - Apr 2013

Keywords

  • Cations
  • Electrochemistry
  • Oxidation
  • Reactive intermediates
  • Sulfur

ASJC Scopus subject areas

  • Organic Chemistry

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    Matsumoto, K., Sanada, T., Shimazaki, H., Shimada, K., Hagiwara, S., Fujie, S., Ashikari, Y., Suga, S., Kashimura, S., & Yoshida, J. I. (2013). The Addition of ArSSAr to Alkenes: The Implications of a Cationic Chain Mechanism Initiated by Electrogenerated ArS(ArSSAr)+. Asian Journal of Organic Chemistry, 2(4), 325-329. https://doi.org/10.1002/ajoc.201300017