Facile and Mild Displacement of Nitrite Ions in Electron-Deficient Nitroarenes by Alkyl or Aryl Thiols in the Presence of Magnesium Methoxide as a Solid Base Catalyst

Hossein Naeimi; Mohsen Moradian

doi:10.1055/s-0032-1317079

Synlett, Table of Contents

Synlett 2012; 23(15): 2223-2226
DOI: 10.1055/s-0032-1317079

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Facile and Mild Displacement of Nitrite Ions in Electron-Deficient Nitroarenes by Alkyl or Aryl Thiols in the Presence of Magnesium Methoxide as a Solid Base Catalyst

Hossein Naeimi*

Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317, Iran, Fax: +98(361)5912397 Email: naeimi@kashanu.ac.ir

,

Mohsen Moradian

Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317, Iran, Fax: +98(361)5912397 Email: naeimi@kashanu.ac.ir

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Abstract

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Abstract

The nucleophilic aromatic substitution reaction (S_NAr) between nitroarenes (having electron-withdrawing groups in the ortho or para position), and alkyl- or arylthiols using magnesium methoxide as a solid base catalyst is described. This method leads to the creation of a series of valuable compounds from arylsulfides via nucleophilic displacement of the nitro group with the sulfanyl moiety. This facile method is a synthetically useful process, and it is significant that the nucleophile is promoted effectively by magnesium methoxide as a base in N,N-dimethylformamide. The displacement of then nitrite ion occurred in the presence of a variety of functional groups that caused an electron-deficient ring such as aldehyde, ketone, ester, cyano, and nitro groups.

Key words

nitroarene - thiol - magnesium methoxide - aryl thioether

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References

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