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

Fingerprint

Electrochemistry
Alkenes
Carbon
Ions
Acetals
Nucleophiles
Alkynes
Electrochemical oxidation
Disulfides
triethylamine
allylsilane
ketene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry. / Fujie, Shunsuke; Matsumoto, Kouichi; Suga, Seiji; Nokami, Toshiki; Yoshida, Jun ichi.

In: Tetrahedron, Vol. 66, No. 15, 10.04.2010, p. 2823-2829.

Research output: Contribution to journalArticle

Fujie, S, Matsumoto, K, Suga, S, Nokami, T & Yoshida, JI 2010, 'Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry', Tetrahedron, vol. 66, no. 15, pp. 2823-2829. https://doi.org/10.1016/j.tet.2010.02.049
Fujie, Shunsuke ; Matsumoto, Kouichi ; Suga, Seiji ; Nokami, Toshiki ; Yoshida, Jun ichi. / Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry. In: Tetrahedron. 2010 ; Vol. 66, No. 15. pp. 2823-2829.
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