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

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

26 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

Access to Document

10.1002/ajoc.201300017

Cite this

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

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.",

keywords = "Cations, Electrochemistry, Oxidation, Reactive intermediates, Sulfur",

author = "Kouichi Matsumoto and Tomonari Sanada and Hayato Shimazaki and Kazuaki Shimada and Shino Hagiwara and Shunsuke Fujie and Yosuke Ashikari and Seiji Suga and Shigenori Kashimura and Yoshida, {Jun ichi}",

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T2 - The Implications of a Cationic Chain Mechanism Initiated by Electrogenerated ArS(ArSSAr)+

AU - Matsumoto, Kouichi

AU - Sanada, Tomonari

AU - Shimazaki, Hayato

AU - Shimada, Kazuaki

AU - Hagiwara, Shino

AU - Fujie, Shunsuke

AU - Ashikari, Yosuke

AU - Suga, Seiji

AU - Kashimura, Shigenori

AU - Yoshida, Jun ichi

PY - 2013/4

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KW - Electrochemistry

KW - Oxidation

KW - Reactive intermediates

KW - Sulfur

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