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

Fingerprint

Electrochemistry

Alkenes

Carbon

Ions

Acetals

Nucleophiles

Alkynes

Electrochemical oxidation

Disulfides

triethylamine

allylsilane

ketene

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

Cite this

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

Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry. / Fujie, Shunsuke; Matsumoto, Kouichi; Suga, Seiji; Nokami, Toshiki; Yoshida, Jun ichi.

In: Tetrahedron, Vol. 66, No. 15, 10.04.2010, p. 2823-2829.

Research output: Contribution to journal › Article

Fujie, S, Matsumoto, K, Suga, S, Nokami, T & Yoshida, JI 2010, 'Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry', Tetrahedron, vol. 66, no. 15, pp. 2823-2829. https://doi.org/10.1016/j.tet.2010.02.049

Fujie S, Matsumoto K, Suga S, Nokami T, Yoshida JI. Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry. Tetrahedron. 2010 Apr 10;66(15):2823-2829. https://doi.org/10.1016/j.tet.2010.02.049

Fujie, Shunsuke ; Matsumoto, Kouichi ; Suga, Seiji ; Nokami, Toshiki ; Yoshida, Jun ichi. / Addition of ArSSAr to carbon-carbon multiple bonds using electrochemistry. In: Tetrahedron. 2010 ; Vol. 66, No. 15. pp. 2823-2829.

@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 = "4",

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 -

Access to Document

10.1016/j.tet.2010.02.049