Nucleophilic aromatic substitution reaction of nitroarenes with alkyl- or arylthio groups in dimethyl sulfoxide by means of cesium carbonate

Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

Treatment of nitroarenes having electron-withdrawing groups at the ortho or para position with alkanethiol in the presence of cesium carbonate in dimethyl sulfoxide at 25°C leads to nucleophilic displacement of the nitro group with the alkylthio group. Cesium carbonate is superior to other bases such as potassium carbonate, sodium carbonate, and triethylamine. The cesium-mediated nucleophilic aromatic substitution reaction provides a mild yet powerful and user-friendly protocol for the synthesis of aryl sulfides.

Original languageEnglish
Pages (from-to)2357-2360
Number of pages4
JournalTetrahedron
Volume62
Issue number10
DOIs
Publication statusPublished - 2006 Mar 6
Externally publishedYes

Keywords

  • Cesium
  • Nitroarene
  • Nucleophilic aromatic substitution reaction
  • Sulfide
  • Thiol

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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