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

Abstract

The nucleophilic aromatic substitution reaction (S N Ar) 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.