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

doi:10.1016/j.tetlet.2003.08.080

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

Research output: Contribution to journal › Article › peer-review

113 Scopus citations

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 language	English (US)
Pages (from-to)	7783-7787
Number of pages	5
Journal	Tetrahedron Letters
Volume	44
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2003.08.080
State	Published - Oct 13 2003
Externally published	Yes

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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title = "Chemoselective reduction of aromatic nitro and azo compounds in ionic liquids using zinc and ammonium salts",

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.",

keywords = "Anilines, Azo compounds, Hydrazobenzenes, Ionic liquids, Nitroarenes, Reduction, Zinc",

author = "Khan, {Faiz Ahmed} and Jyotirmayee Dash and Ch Sudheer and Gupta, {Rakesh Kumar}",

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. ",

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AU - Khan, Faiz Ahmed

AU - Dash, Jyotirmayee

AU - Sudheer, Ch

AU - Gupta, Rakesh Kumar

N1 - 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.

PY - 2003/10/13

Y1 - 2003/10/13

N2 - 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.

AB - 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.

KW - Anilines

KW - Azo compounds

KW - Hydrazobenzenes

KW - Ionic liquids

KW - Nitroarenes

KW - Reduction

KW - Zinc

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SN - 0040-4039

VL - 44

SP - 7783

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

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

Abstract

Bibliographical note

Keywords

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