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

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

Access to Document

10.1016/j.tet.2010.02.049

Fingerprint Dive into the research topics of 'Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry'. Together they form a unique fingerprint.

Cite this

@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}",

year = "2010",

month = apr,

day = "10",

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

language = "English",

volume = "66",

pages = "2823--2829",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "15",

}

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

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.

UR - http://www.scopus.com/inward/record.url?scp=77949261533&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77949261533&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2010.02.049

DO - 10.1016/j.tet.2010.02.049

M3 - Article

AN - SCOPUS:77949261533

VL - 66

SP - 2823

EP - 2829

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 15

ER -