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

doi:10.1002/ajoc.201300017

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

Okayama University

Research output: Contribution to journal › Article › peer-review

25 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 language	English
Pages (from-to)	325-329
Number of pages	5
Journal	Asian Journal of Organic Chemistry
Volume	2
Issue number	4
DOIs	https://doi.org/10.1002/ajoc.201300017
Publication status	Published - Apr 2013

Keywords

Cations
Electrochemistry
Oxidation
Reactive intermediates
Sulfur

ASJC Scopus subject areas

Organic Chemistry

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10.1002/ajoc.201300017

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The Addition of ArSSAr to Alkenes : The Implications of a Cationic Chain Mechanism Initiated by Electrogenerated ArS(ArSSAr)⁺. / Matsumoto, Kouichi; Sanada, Tomonari; Shimazaki, Hayato; Shimada, Kazuaki; Hagiwara, Shino; Fujie, Shunsuke; Ashikari, Yosuke; Suga, Seiji; Kashimura, Shigenori; Yoshida, Jun ichi.

In: Asian Journal of Organic Chemistry, Vol. 2, No. 4, 04.2013, p. 325-329.

Research output: Contribution to journal › Article › peer-review

Matsumoto, Kouichi ; Sanada, Tomonari ; Shimazaki, Hayato ; Shimada, Kazuaki ; Hagiwara, Shino ; Fujie, Shunsuke ; Ashikari, Yosuke ; Suga, Seiji ; Kashimura, Shigenori ; Yoshida, Jun ichi. / The Addition of ArSSAr to Alkenes : The Implications of a Cationic Chain Mechanism Initiated by Electrogenerated ArS(ArSSAr)⁺. In: Asian Journal of Organic Chemistry. 2013 ; Vol. 2, No. 4. pp. 325-329.

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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.",

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