Addition of ArSSAr to carbon–carbon multiple bonds using electrochemistry

• Fujie, Shunsuke

• Matsumoto, Kouichi

• Suga, Seiji

• Nokami, Toshiki

• Yoshida, Jun-ichi

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.

Journal

• Tetrahedron

  Tetrahedron 66 (15), 2823-2829, 2010-04-10

  Elsevier

Keywords

• Organic Chemistry
• Drug Discovery
• Biochemistry

Details

• CRID: 1050001202112315264
• NII Article ID: 120002141660
• NII Book ID: AA00861787
• ISSN: 00404020
• DOI: 10.1016/j.tet.2010.02.049
• HANDLE: 2433/113884
• Web Site: https://api.elsevier.com/content/article/PII:S0040402010002516?httpAccept=text/xml
• Web Site: https://api.elsevier.com/content/article/PII:S0040402010002516?httpAccept=text/plain
• Text Lang: en
• Article Type: journal article
• Data Source:
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  • Crossref
  • CiNii Articles
  • KAKEN