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 › peer-review

31 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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@article{d124d3e79bd8470ab12a5109dc1d019b,

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}",

note = "Funding Information: This work was financially supported in part by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science . K.M. acknowledges JSPS for financial support. ",

year = "2010",

month = apr,

day = "10",

doi = "10.1016/j.tet.2010.02.049",

language = "English",

volume = "66",

pages = "2823--2829",

journal = "Tetrahedron",

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publisher = "Elsevier Limited",

number = "15",

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TY - JOUR

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

N1 - Funding Information: This work was financially supported in part by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science . K.M. acknowledges JSPS for financial support.

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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DO - 10.1016/j.tet.2010.02.049

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VL - 66

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JO - Tetrahedron

JF - Tetrahedron

IS - 15

ER -

Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry

Abstract

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