Palladium‐catalyzed reduction of nitroaromatic compounds to the corresponding anilines

Mirza‐Aghayan, Maryam; Boukherroub, Rabah; Rahimifard, Mahshid; Bolourtchian, Mohammad

doi:10.1002/aoc.1645

Cited by 26 publications

(14 citation statements)

References 41 publications

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“…The reduction of 4-NP is also necessary for the manufacture of analgesic, antipyretic and other drugs, in pharmaceutical industries. [19] In addition this reaction has been widely exploited for confirming the synthesis of efficient nanoparticle catalyst by the study of catalytic activities of nanoparticles. [20] The selective oxidation of alcohols to the corresponding carbonyl compounds has been comprehensively studied, due to their importance in production of fine chemicals and intermediates.…”

Section: Introductionmentioning

confidence: 99%

Ag‐nanoparticle embedded p(AA) hydrogel as an efficient green heterogeneous Nano‐catalyst for oxidation and reduction of organic compounds

Ghorbanloo

Heydari

Yahiro

2017

Applied Organom Chemis

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P(AA)‐Ag heterogeneous catalyst system comprised of Ag nanoparticles embedded within hydrogel matrices has been described for the selective aerobic oxidation of alcohols and reduction of nitro phenols in water. P(AA)‐Ag nanocomposite was characterized by Fourier transform infrared (FT‐IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermal gravimetric analysis (TGA), X‐Ray photoelectron spectroscopy (XPS) and inductively coupled plasma atomic emission spectrometer (ICP). Catalytic activity of p(AA)‐Ag catalyst was investigated in the aerobic oxidation of primary alcohols and reduction of nitro compounds by emphasizing the effect of different parameters such as temperature, catalyst amount, substituent effect, etc. The catalyst was easily recovered from the reaction medium and it could be re‐used for other three runs without significant loss of activity.

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Section: Introductionmentioning

confidence: 99%

Ag‐nanoparticle embedded p(AA) hydrogel as an efficient green heterogeneous Nano‐catalyst for oxidation and reduction of organic compounds

Ghorbanloo

Heydari

Yahiro

2017

Applied Organom Chemis

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Section: Introductionmentioning

confidence: 99%

“…Aromatic amines are important compounds in pharmaceutical and agrochemical industries . Because of significant biological activities, aromatic amines are used in a range of applications, from natural products to medical agents . A wide range of applications of these compounds leads to the development of several protocols for C‐N bond formation over the years .…”

Section: Introductionmentioning

confidence: 99%

Immobilization of nickel ions onto the magnetic nanocomposite based on cross‐linked melamine groups: Effective heterogeneous catalyst for N‐Arylation of Arylboronic acids

Pourjavadi

Keshavarzi

Moghaddam

et al. 2017

Applied Organom Chemis

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A new magnetic heterogeneous catalyst was synthesized by immobilization of nickel ions onto a cross‐linked polymeric nanocomposite composed of cyanuric chloride, ethylenediamine and functionalized magnetic nanoparticles. The resulting nitrogen rich support was capable of adsorbing large amounts of nickel ions (1.20 mmol g−1). The synthesized catalyst was characterized using AAS, TEM, FT‐IR, EDX, TGA, SEM, BET and XRD techniques. The performance of the prepared catalyst was investigated in the C‐N coupling of arylamines with aryl boronic acids. The reaction was carried out under a mild condition and good to moderate to good yields of products was obtained using only 5.0 mol% of the catalyst. The catalyst was easily recovered and reused for at least 7 times without any significant loss of its activity.

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“…The exposure to 4‐NA is very harmful for human beings and causes dyspnea (breathing difficulty), irritability, vomiting, diarrhoea, convulsions, respiratory arrest, anaemia, and jaundice, etc. Therefore, reduction of 4‐NA into p ‐phenylenediamine (pPDA) is of great importance . The product of the catalytic reduction, i.e., pPDA is an important dye and has many industrial applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of inorganic–organic polymer microgels for catalytic reduction of 4‐nitroaniline in aqueous medium

et al. 2016

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Poly(N‐isopropylacrylamide‐co‐acrylic acid) [p(NiPA‐co‐AAc)] microgel particles were synthesized by free radical precipitation polymerization in aqueous medium. Silver nanoparticles (Ag NPs) were fabricated inside the microgels by in situ reduction method. UV–visible, Fourier transform infrared (FTIR), and dynamic light scattering techniques were used for characterization of pure microgels. The Ag‐p(NiPA‐co‐AAc) hybrid microgels were characterized by UV–visible, FTIR, X‐ray diffraction, and transmission electron microscopy. The hybrid microgel system was used as a catalyst for reduction of 4‐nitroaniline (4‐NA) in aqueous medium. The kinetics of the catalytic reduction of 4‐NA under various conditions of concentration of hybrid microgels, sodium borohydride (NaBH4), and 4‐NA was monitored by UV–visible spectrophotometry. It was found that the value of apparent rate constant (kapp) increases with increase of concentration of NaBH4 and catalyst dosage while it remains constant at various concentrations of 4‐NA. The kinetic data were used to elaborate the conversion of 4‐NA into p‐phenylenediamine on the basis of electron relaying effect of Ag NPs present inside the microgels. POLYM. COMPOS., 39:645–653, 2018. © 2016 Society of Plastics Engineers

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Palladium‐catalyzed reduction of nitroaromatic compounds to the corresponding anilines

Abstract: aReduction of a variety of nitroaromatic compounds with triethylsilane in the presence of catalytic amounts of palladium chloride in ethanol resulted in the formation of the corresponding anilines in excellent yields.

Cited by 26 publications

References 41 publications

Ag‐nanoparticle embedded p(AA) hydrogel as an efficient green heterogeneous Nano‐catalyst for oxidation and reduction of organic compounds

Ag‐nanoparticle embedded p(AA) hydrogel as an efficient green heterogeneous Nano‐catalyst for oxidation and reduction of organic compounds

Immobilization of nickel ions onto the magnetic nanocomposite based on cross‐linked melamine groups: Effective heterogeneous catalyst for N‐Arylation of Arylboronic acids

Synthesis and characterization of inorganic–organic polymer microgels for catalytic reduction of 4‐nitroaniline in aqueous medium

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