“Rapid and Inexpensive Method for Reduction of Nitroarenes to Anilines”

Desai, D. G.; Swami, S. S.; Hapase, S. B.

doi:10.1080/00397919908086068

Cited by 28 publications

(11 citation statements)

References 6 publications

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“…Nowadays, numerous methods for the reduction of aromatic nitro have been reported in the literatures, such as catalytic hydrogenation [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20], catalytic transfer hydrogenation [21][22][23][24][25][26][27][28][29], CO/H 2 O conditions [30][31][32] and other reduction systems [33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48]. The important developed catalytic systems are listed as follows, MCM-41-silylamine palladium(II)/THF [5],poly(4-vinylpyridine-co-N-vinylpyrrolidone)-Pd (0)/EtOH [6], Au/SiO 2 /EtOH [7], nanosized nickel/EtOH [8], Au-Pt-NH 2 -Si-MCM-41/CH 3 O...…”

Section: Introductionmentioning

confidence: 99%

A Green Reduction of Aromatic Nitro Compounds to Aromatic Amines Over a Novel Ni/SiO2 Catalyst Passivated with a Gas Mixture

Zheng

Wang

et al. 2008

Catal Lett

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An efficient, mild and practical method for the reduction of aromatic nitro compounds using Ni/SiO 2 as catalyst is reported. The catalyst has been prepared and characterized by XRD, FT-IR, TEM, SEM successfully. The Ni loading is about 55 wt.%. The prominent merit of the Ni/SiO 2 catalyst passivated with a gas mixture is that it can be stored safely in air below 423 K and needs no activation before use. In the catalytic test, Ni/SiO 2 is found to be a highly efficient and reusable catalyst for the reduction of various aromatic nitro compounds. This catalyst is applicable for the preparation of various aromatic amines with different groups, the conversion and selectivity are almost up to 100%. Moreover, it is inexpensive, can be prepared and scaled up easily.

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Section: Introductionmentioning

confidence: 99%

A Green Reduction of Aromatic Nitro Compounds to Aromatic Amines Over a Novel Ni/SiO2 Catalyst Passivated with a Gas Mixture

Zheng

Wang

et al. 2008

Catal Lett

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“…A number of experiments were conducted to give some insights into the mechanism. In principle, a nitroarene can be reduced by zinc to form an aniline 32 33 , which can then undergoes N -alkylation with an alkyl halide to form the alkyl aryl amine product 7 . Indeed, it was found that in the absence of an alkyl halide, 4-nitrotoluene was reduced under the coupling conditions to form 4-methylaniline, albeit in a modest yield ( Fig.…”

Section: Resultsmentioning

confidence: 99%

Amine synthesis via iron-catalysed reductive coupling of nitroarenes with alkyl halides

Cheung

2016

Nat Commun

139

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(Hetero)Aryl amines, an important class of organic molecules in medicinal chemistry, are most commonly synthesized from anilines, which are in turn synthesized by hydrogenation of nitroarenes. Amine synthesis directly from nitroarenes is attractive due to improved step economy and functional group compatibility. Despite these potential advantages, there is yet no general method for the synthesis of (hetero)aryl amines by carbon–nitrogen cross-coupling of nitroarenes. Here we report the reductive coupling of nitroarenes with alkyl halides to yield (hetero)aryl amines. A simple iron catalyst enables the coupling with numerous primary, secondary and tertiary alkyl halides. Broad scope and high functional group tolerance are demonstrated. Mechanistic study suggests that nitrosoarenes and alkyl radicals are involved as intermediates. This new C–N coupling method provides general and step-economical access to aryl amines.

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“…2‐Azido‐4‐isopropyl‐1‐methylbenzene ( 9 , Scheme ) was synthesized in a two‐step procedure. Firstly, commercially available 2‐nitro‐ p ‐cymene ( 16 ) was reduced to its corresponding aniline derivative by treatment with a ferric chloride/zinc/dimethyl formamide/H 2 O system 15. The aniline derivative was then treated with hydrochloric acid and sodium nitrite in an ice/salt bath.…”

Section: Resultsmentioning

confidence: 99%

Modular Synthesis of Triazole‐Containing Triaryl α‐Helix Mimetics

et al. 2011

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We describe novel scaffold designs for nonpeptidic α‐helix mimetics. The tricyclic scaffolds contain triazoles and reproduce amino acid side chains i, i+3, and i+7. The three different scaffolds are synthetically readily accessible, allow the introduction of further substituents to increase the versatility, and are suitable for library design. A modular synthesis route using CuI‐ and RuII‐catalyzed azide–alkyne [3+2] cycloadditions as central steps was developed. To demonstrate the methodology, we have prepared a library of compounds containing all three scaffolds.

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“Rapid and Inexpensive Method for Reduction of Nitroarenes to Anilines”

Cited by 28 publications

References 6 publications

A Green Reduction of Aromatic Nitro Compounds to Aromatic Amines Over a Novel Ni/SiO2 Catalyst Passivated with a Gas Mixture

A Green Reduction of Aromatic Nitro Compounds to Aromatic Amines Over a Novel Ni/SiO2 Catalyst Passivated with a Gas Mixture

Amine synthesis via iron-catalysed reductive coupling of nitroarenes with alkyl halides

Modular Synthesis of Triazole‐Containing Triaryl α‐Helix Mimetics

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