Chemoselective reduction of aromatic nitro and azo compounds in ionic liquids using zinc and ammonium salts

Faiz Ahmed Khan, Jyotirmayee Dash, Ch Sudheer, Rakesh Kumar Gupta

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Abstract

Nitroarenes were chemoselectively reduced to the corresponding amines using zinc and aqueous ammonium salts in ionic liquids as a safe and recyclable reaction medium. Our results specify the effect of ammonium salts in the process; the combination of Zn/NH4Cl in [bmim][PF6] or Zn/HCO2NH4 in [bmim][BF4] were the suitable conditions for the reduction of nitroarenes. Azobenzenes were also smoothly reduced to hydrazobenzenes with Zn/HCO2NH4 (aq.) in recyclable [bmim][BF4] without any over reduction to the corresponding anilines.

Original languageEnglish (US)
Pages (from-to)7783-7787
Number of pages5
JournalTetrahedron Letters
Volume44
Issue number42
DOIs
StatePublished - Oct 13 2003

Keywords

  • Anilines
  • Azo compounds
  • Hydrazobenzenes
  • Ionic liquids
  • Nitroarenes
  • Reduction
  • Zinc

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