Cu nanoparticles embedded on reticular chitosan-derived N-doped carbon: Application to the catalytic hydrogenation of alkenes, alkynes and N-heteroarenes

Hammi, Nisrine; Chen, Shuo; Michon, Christophe; Royer, Sébastien; Kadib, Abdelkrim El

doi:10.1016/j.mcat.2021.112104

Cited by 5 publications

(4 citation statements)

References 68 publications

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“…Hammi et al used CuNPs embedded on reticular chitosan-derived nitrogen-doped carbon (CuNC-1-700) for the reductive hydrogenation of nitrogen-containing heteroarenes ( 32 / 34 / 36 / 38 / 40 / 42 ; Scheme 9 ) to give the hydrogenated counterparts at 80 °C. 63a The present catalysts were also used with alkenes and alkynes, and the reactions proceeded with more than 99% yields. These NCs have been prepared from melamine, chitosan, ethylenediaminetetraacetic acid and copper salts via sequential hydrothermal and pyrolysis at 700 °C.…”

Section: Aza- and Oxa-heterocycle Synthesis Catalysed By Mnpsmentioning

confidence: 92%

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

Dhameliya,

Shah,

Shah

et al. 2024

Synlett

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The versatility of aza- and oxa-heterocyclic compounds has garnered significant attention in recent times. A large number of currently approved pharmaceutical products include nitrogen- and oxygen-containing heterocycles. Recent nanotechnological developments have propelled an upsurge in the applications of nanocatalysis for heterocyclic synthesis. Metal nanoparticles (MNPs) have emerged as promising catalysts for the synthesis of aza- and oxa-heterocycles owing to their unique physicochemical properties. Various MNPs including gold, silver, nickel and palladium have been evaluated for their catalytic activities in different reaction types, including cyclisation, coupling, hydrogenation and oxidative transformations. The MNPs have exhibited remarkable catalytic efficiency when utilised under optimal conditions. These catalysts have showcased high reusability and recyclability, yielding satisfactory amounts of the desired heterocyclic compound. The present work provides a detailed overview of recent advances in the area of MNP-assisted synthetic construction of aza- and oxa-heterocycles, published during the previous calendar year, 2022. The review serves as a valuable resource and also paves the way for future investigations in the development of novel catalytic strategies for heterocycle synthesis.1 Introduction2 Nanocatalysis3 Aza- and Oxa-Heterocycle Synthesis Catalysed by MNPs3.1 AuNPs3.2 CuNPs3.3 CoNPs3.4 FeNPs3.5 NiNPs3.6 PdNPs3.7 PtNPs3.8 SiNPs3.9 ZnNPs3.10 Bimetallic NPs3.11 Other MNPs4 Summary and Outlook

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Section: Aza- and Oxa-heterocycle Synthesis Catalysed By Mnpsmentioning

confidence: 92%

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

Dhameliya,

Shah,

Shah

et al. 2024

Synlett

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“…Multiple synthetic procedures, alone or combined, have been used to convert chitosan into N-doped carbon materials . They include hydrothermal treatment, pyrolysis under an inert atmosphere, , and microwave-assisted treatment . Given the thermally induced evolution of the chitosan skeleton during pyrolysis, precise control of the experimental parameters is crucial.…”

Section: Introductionmentioning

confidence: 99%

Cellulose Conversion to Glycols over a Carbon-Supported Ni–W_xC Nanocatalyst: The N-Doping Effect on Catalyst Stability

Boulos,

Goc,

Perret

et al. 2024

ACS Appl. Nano Mater.

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Cellulose is an attractive nonedible feedstock for the production of chemicals, especially through metal catalysis. However, its hydrothermal catalytic conversion induces severe deactivation of catalysts, notably by metal leaching and structure sintering. In this work, we studied a series of nickel-and tungstenbased catalysts supported on porous carbon (C) or N-doped porous carbon (NC). These catalysts were formed from nanosized bimetallic particles of Ni and W supported on porous N-doped carbon supports. The supports were prepared by hydrothermal conversion of N-containing biopolymers, followed by pyrolysis under an inert atmosphere. The bimetallic nanoparticles were deposited by wet impregnation. The idea was to study the influence of Ndoping of the support on the stability during the catalysis of the metal nanoparticles on the support. For instance, an amorphous nitrogen-doped carbon with a hierarchical porosity and a surface area up to 286 m 2 •g −1 was obtained from the hydrothermal pyrolysis of chitosan, and, depending on the activation atmosphere (H 2 or N 2 ), metal particles in the 15−30 nm size were obtained. Regarding the application to cellulose conversion, molar yields up to 20% in ethylene glycol and 8% in propylene glycol were obtained by a reaction at 245 °C for 1 h using a nitrogen-activated catalyst. When the catalyst was activated under hydrogen, the ethylene glycol yield was increased to 51% while the propylene glycol yield remained low. Very interestingly, the presence of Ncontaining moieties within the carbon supports proved an interest by increasing the catalyst stability during successive reaction cycles. The ethylene glycol yield remained stable during 3 reaction cycles for the N-doped catalyst, as compared to the nondoped one, which presented an important deactivation after 3 cycles.

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“…Thus, developing versatile catalysts with high catalytic activity at a low cost is of great importance . In the last decade, the use of earth-abundant 3d metals in catalysis has resurfaced to provide alternatives to noble metals for ring hydrogenation of (hetero)arenes. − For example, the group of Beller developed remarkably supported nanostructured Ni, , Co, ,− and Fe nanoparticles, including easily accessible Mn(CO) 5 Br as a homogeneous catalyst that exhibits higher activity and chemoselectivity for hydrogenation of N -heterocycles . However, the use of expensive organic ligands and catalyst supports is the main disadvantage of these catalytic systems.…”

Section: Introductionmentioning

confidence: 99%

Earth-Abundant Heterogeneous Cobalt Catalyst for Selective Ring Hydrogenation of (Hetero)arenes and Gram-Scale Synthesis of Pharmaceutical Intermediates

et al. 2023

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It is highly desired but scientifically as well as technologically challenging to develop non-noble metal-based hydrogenation catalysts that can substitute noble metal-based ones. Herein, we present a facile and environmentally friendly approach for synthesizing pine needle biomassderived nitrogen-doped carbon-supported Co 3 O 4 nanoparticles (Co 3 O 4 / PNC). The whole process involves the impregnation of pine needles with cobalt nitrate salt and subsequent pyrolysis at 500 °C under a nitrogen atmosphere. Applying this Co 3 O 4 /PNC nanocatalyst, a broad range of substituted phenols and functional organic chemicals, including N-and Oheteroarenes, could be efficiently transformed into their corresponding ringhydrogenated products in good-to-excellent yields (>55 examples). In addition, this catalytic approach has proved useful for the preparation of seven key drug intermediates on a gram scale, which are commonly used in manufacturing active pharmaceutical ingredients in bulk quantities. Advantageously, cyclohexanecarboxylic acid, a key pharmaceutical building block of praziquantel, was synthesized from polystyrene in a two-step process. The pivotal physicochemical properties of fresh and spent Co 3 O 4 /PNC nanocatalysts were thoroughly investigated by high-resolution transmission electron microscopy, X-ray photoelectron spectroscopy, X-ray diffraction, N 2 adsorption−desorption, Raman analysis, H 2 -temperature programmed reduction, and CO 2 -temperature-programmed desorption analysis. The cobalt content in the Co 3 O 4 /PNC nanocatalyst was estimated by inductively coupled plasma atomic emission spectroscopy analysis. Besides, the Co 3 O 4 /PNC nanocatalyst is stable, easily recovered, and reused effectively for four catalytic cycles with no loss of activity or selectivity. Furthermore, density functional theory calculations were performed to get more insights into the reaction mechanism.

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Cu nanoparticles embedded on reticular chitosan-derived N-doped carbon: Application to the catalytic hydrogenation of alkenes, alkynes and N-heteroarenes

Cited by 5 publications

References 68 publications

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

Cellulose Conversion to Glycols over a Carbon-Supported Ni–W_xC Nanocatalyst: The N-Doping Effect on Catalyst Stability

Earth-Abundant Heterogeneous Cobalt Catalyst for Selective Ring Hydrogenation of (Hetero)arenes and Gram-Scale Synthesis of Pharmaceutical Intermediates

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Cu nanoparticles embedded on reticular chitosan-derived N-doped carbon: Application to the catalytic hydrogenation of alkenes, alkynes and N-heteroarenes

Cited by 5 publications

References 68 publications

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

Synthesis of Nitrogen- and Oxygen-Containing Heterocycles Catalysed by Metal Nanoparticles Reported in 2022

Cellulose Conversion to Glycols over a Carbon-Supported Ni–WxC Nanocatalyst: The N-Doping Effect on Catalyst Stability

Earth-Abundant Heterogeneous Cobalt Catalyst for Selective Ring Hydrogenation of (Hetero)arenes and Gram-Scale Synthesis of Pharmaceutical Intermediates

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Product

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Cellulose Conversion to Glycols over a Carbon-Supported Ni–W_xC Nanocatalyst: The N-Doping Effect on Catalyst Stability