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

Bibliographical note

Funding Information:
We thank the Department of Science and Technology (DST), the Council of Scientific and Industrial Research (CSIR), New Delhi for financial assistance. J.D., R.K.G. and C.S. thank CSIR, U.G.C. for fellowships.

Keywords

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

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