Direct hydrogenation and one-pot reductive amidation of nitro compounds over Pd/ZnO nanoparticles as a recyclable and heterogeneous catalyst

Hosseini‐Sarvari, Mona; Razmi, Zahra

doi:10.1016/j.apsusc.2014.10.131

Cited by 22 publications

(7 citation statements)

References 73 publications

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“…), , reducing agents, high pressure, and multiple solvents. − Li et al used a Pt wire-based catalyst for the amidation of nitroarenes . Sarvari et al used Pd/ZnO nanoparticles for the reductive amidation of nitro compounds . Zeynizadeh et al used Cu and Ni-based catalysts for the direct acetylation of nitro and amine derivatives, and Shokri et al used Fe 3 O 4 @Cu( OH ) x nanoparticles for the reductive acetylation of nitroarenes …”

Section: Introductionmentioning

confidence: 99%

“…26 Sarvari et al used Pd/ZnO nanoparticles for the reductive amidation of nitro compounds. 27 Zeynizadeh et al used Cu and Ni-based catalysts for the direct acetylation of nitro and amine derivatives, 28 and Shokri et al used Fe 3 O 4 @Cu(OH) x nanoparticles for the reductive acetylation of nitroarenes. 29 Therefore, in the search for an alternative methodology that requires lesser reaction steps, time, and solvent, low-cost nanomaterials/catalysts are always desirable.…”

Section: ■ Introductionmentioning

confidence: 99%

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Waste-Derived Iron Nanoparticles for Solvent-Free Single-Step Reductive Acetylation of Nitroarenes

Kaushik,

Sharma,

Twinkle

et al. 2023

ACS Sustainable Chem. Eng.

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A simple and single-step synthetic protocol is reported here for synthesizing medicinally important amide compounds such as acetanilide (N-phenylacetamide) and its derivatives (including paracetamol and phenacetin). Compared to the existing reports used for a single-step amidation that requires multiple reagents, herein, waste-derived iron nanoparticles (FeO x -NPs) isolated from the "free-of-cost available iron dust/powder" were used for the same single-step amidation reaction without using any external reagents and high pressure, resulting in the costeffective viable reported procedure. The Soxhlet-purified iron dust is subjected to high-temperature heating at ∼800 °C in a muffle furnace to achieve its heterogeneously active form (Fe 3 O 4 -type moieties on its surface). The as-prepared catalyst (FeO x -NPs) has been used to synthesize 17 acetanilide derivatives including two essential antipyretic drugs, paracetamol and phenacetin, on a gram scale, and one industrially important dye/pigment precursor (2-nitroacetanilide). Based on the X-ray photoelectron spectroscopy and vibrating sample magnetometry results, a possible mechanism has been proposed. The sustainability associated with the whole process is the direct amide formation using a magnetically separable waste-derived metal catalyst in solvent-free conditions, which provides a possible way to utilize large-scale industrial waste, thus directly reducing some environmental stress.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Waste-Derived Iron Nanoparticles for Solvent-Free Single-Step Reductive Acetylation of Nitroarenes

Kaushik,

Sharma,

Twinkle

et al. 2023

ACS Sustainable Chem. Eng.

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“…), ([KSCOCH 3 ]/DMF/130°C), ([KSCOCH 3 ‐(Triton‐X 405)]/solvent‐free/130°C), ([(Pt/ZrO 2 )–Ac 2 O]/CH 3 OH/r.t. ), ([Na 2 SO 3 –AcOH]/boiling Ac 2 O), ([(Nano Pd/ZnO)–N 2 H 4 .H 2 O–Ac 2 O]/H 2 O:EtOH/90°C), and ([Fe 3 O 4 @Cu(OH) x ‐NaBH 4 ‐Ac 2 O]/H 2 O/60°C) are available for this mentioned one‐pot reaction. In this regard, introducing new, simple, and practical catalytic protocols for the selective preparation of acetamide derivatives via one‐pot reductive acetylation of nitroarenes is very important in the chemical industry, in particular, for organic synthesis.…”

Section: Resultsmentioning

confidence: 99%

Application of Cu(Hdmg)₂ as a simple and cost‐effective catalyst for the convenient one‐pot reductive acetylation of aromatic nitro compounds

Zeynizadeh

Mousavi

Zarrin

2019

J Chinese Chemical Soc

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In this article, we have developed a novel and simple one‐pot reductive acetylation of aromatic nitro compounds with sodium borohydride (NaBH4) in ethyl acetate (EtOAc) under reflux conditions in the presence of the bis(dimethylglyoximato)copper(II) complex [Cu(Hdmg)2] as an efficient and cost‐effective copper‐containing catalyst. Notably, using the above‐mentioned one‐pot reaction, the corresponding acetamide derivatives were obtained in high to excellent yields.

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“…The catalytic activity of Pd/CVS-ZnO in the reduction of nitroarenes is comparable with the activity of the previously reported Pd/ ZnO catalysts (see Supporting Information, Table S2). 38,40 Additionally, we examined the activity of the catalyst for the hydrodebromination of aryl bromides. The reaction conditions were optimized using 2-bromonaphthalene (6a) as the model substrate.…”

Section: Catalytic Performances Of the Pd/cvs-znomentioning

confidence: 99%

Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts

Kokanović,

Ajdačić,

Terzić Jovanović

et al. 2023

ACS Appl. Nano Mater.

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Herein, we report the synthesis and application of a highly active and versatile Pd/chemical vapor synthesis-ZnO (Pd/CVS-ZnO) catalytic system. The two-step preparation of the catalyst includes chemical vapor synthesis (CVS) of ultrapure ZnO nanotetrapods, followed by the liquid-phase in situ reduction of a Pd precursor and deposition of polycrystalline Pd nanoparticles (∼6 nm). The as-synthesized catalyst was characterized using standard instrumental techniques. The catalyst was successfully applied in four chemical reactions: Suzuki–Miyaura cross-coupling, reduction of nitroarenes, decarbonylation, and hydrodebromination of aromatic compounds, of which, the latter two are reported for the first time for the Pd/ZnO catalytic system. The catalyst showed excellent activity within a wide range of substrates, delivering the products in high yields (70–99%). The recyclability of the Pd/CVS-ZnO catalyst was tested through two different approaches. First, the catalyst recyclability was examined in all four reactions, reusing the catalyst up to four times in the Suzuki–Miyaura cross-coupling reaction, as well as the reduction of 4-nitrobenzonitrile, without a significant loss of yield. Furthermore, the catalyst was successively used in three different reactions, showing a high degree of stability and delivering excellent product yields in all cases. In addition to its excellent activity, versatility, and stability, the Pd/CVS-ZnO catalytic system also exhibits excellent recyclability over consecutive runs, which makes it a promising candidate for future application in complex industrial processes.

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Direct hydrogenation and one-pot reductive amidation of nitro compounds over Pd/ZnO nanoparticles as a recyclable and heterogeneous catalyst

Cited by 22 publications

References 73 publications

Waste-Derived Iron Nanoparticles for Solvent-Free Single-Step Reductive Acetylation of Nitroarenes

Waste-Derived Iron Nanoparticles for Solvent-Free Single-Step Reductive Acetylation of Nitroarenes

Application of Cu(Hdmg)₂ as a simple and cost‐effective catalyst for the convenient one‐pot reductive acetylation of aromatic nitro compounds

Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts

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Direct hydrogenation and one-pot reductive amidation of nitro compounds over Pd/ZnO nanoparticles as a recyclable and heterogeneous catalyst

Cited by 22 publications

References 73 publications

Waste-Derived Iron Nanoparticles for Solvent-Free Single-Step Reductive Acetylation of Nitroarenes

Waste-Derived Iron Nanoparticles for Solvent-Free Single-Step Reductive Acetylation of Nitroarenes

Application of Cu(Hdmg)2 as a simple and cost‐effective catalyst for the convenient one‐pot reductive acetylation of aromatic nitro compounds

Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts

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Application of Cu(Hdmg)₂ as a simple and cost‐effective catalyst for the convenient one‐pot reductive acetylation of aromatic nitro compounds