Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry

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

doi:10.1016/j.tet.2010.02.049

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 journal › Article

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 language	English
Pages (from-to)	2823-2829
Number of pages	7
Journal	Tetrahedron
Volume	66
Issue number	15
DOIs	https://doi.org/10.1016/j.tet.2010.02.049
Publication status	Published - Apr 10 2010
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Fujie, S., Matsumoto, K., Suga, S., Nokami, T., & Yoshida, J. I. (2010). Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry. Tetrahedron, 66(15), 2823-2829. https://doi.org/10.1016/j.tet.2010.02.049

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title = "Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry",

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.",

author = "Shunsuke Fujie and Kouichi Matsumoto and Seiji Suga and Toshiki Nokami and Yoshida, {Jun ichi}",

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T1 - Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry

AU - Fujie, Shunsuke

AU - Matsumoto, Kouichi

AU - Suga, Seiji

AU - Nokami, Toshiki

AU - Yoshida, Jun ichi

PY - 2010/4/10

Y1 - 2010/4/10

N2 - 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.

AB - 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.

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