Cellulose nanocrystals-Palladium, a novel recyclable catalyst for coupling reaction

Seyednejhad, Sajedeh; Khalilzadeh, Mohammad A.; Sadeghifar, Hasan; Zareyee, Daryoush

doi:10.33945/sami/ecc.2020.3.6

Cited by 7 publications

(4 citation statements)

References 17 publications

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“…Recyclability was limited to 5 successive runs with yield dropping from 97% to 81% and reaction time extending from 20 min to 7 h. Alumina was added in order to supposedly stabilize the hybrid since C-O-Si bonds were said to be easily hydrolyzed. Such instability was however not described by other teams who successfully used C-O-Si bonds in other nanocatalysts [27,28,30,31,66,67].…”

Section: Cellulose Compositesmentioning

confidence: 90%

“…60%). A similar structure, obtained with an isatine moiety [30] or a 2-hydroxynaphthaldehyde moiety [31] instead of the pyridyl, is also an efficient recyclable catalyst. A palladium complex has been immobilized on cellulose via another Schiff base, more precisely a salen-type tridentate ligand, with no silyl spacer (Figure 3a) [32].…”

Section: In Suzuki-miyaura Couplingmentioning

confidence: 99%

“…It demonstrated high efficiency with 94% reaction yield and indicated good performance after four times recovery and reuse. Pd(II) chemically anchored on cellulose nanocrystals via a Schiff base and a silyl spacer was applied for C-O couplings using a series of aryl halide and phenol derivatives [30]. It demonstrated high efficiency with 94% reaction yield and indicated good performance after four times recovery and reuse.…”

Section: In C-heteroatom Couplingmentioning

confidence: 99%

“…the C-O coupling of phenol) with iodobenzene in mild conditions: in DMSO as a solvent, at 80 • C, with K 2 CO 3 as a base, with 78% yield (resp. 93% yield).Pd(II) chemically anchored on cellulose nanocrystals via a Schiff base and a silyl spacer was applied for C-O couplings using a series of aryl halide and phenol derivatives[30]. It demonstrated high efficiency with 94% reaction yield and indicated good performance after four times recovery and reuse.Hydroxypropyl methylcellulose (HPMC) is a food additive used as an emulsifier[94].…”

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confidence: 99%

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Wood-Sourced Polymers as Support for Catalysis by Group 10 Transition Metals

et al. 2022

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Despite providing interesting solutions to reduce the number of synthetic steps, to decrease energy consumption or to generate less waste, therefore contributing to a more sustainable way of producing important chemicals, the expansion of the use of homogeneous catalysis in industrial processes is hampered by several drawbacks. One of the most important is the difficulty to recycle the noble metals generating potential high costs and pollution of the synthesized products by metal traces detrimental to their applications. Supporting the metals on abundant and cheap biosourced polymers has recently appeared as an almost ideal solution: They are much easier to recover from the reaction medium and usually maintain high catalytic activity. The present bibliographical review focuses on the development of catalysts based on group 10 transition metals (nickel, palladium, platinum) supported on biopolymers obtained from wood, such as cellulose, hemicellulose, lignin, and their derivatives. The applications of these catalysts in organic synthesis or depollution are also addressed in this review with examples of C-C couplings, oxidation, or hydrogenation reactions.

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Section: Cellulose Compositesmentioning

confidence: 90%

Section: In Suzuki-miyaura Couplingmentioning

confidence: 99%

Section: In C-heteroatom Couplingmentioning

confidence: 99%

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confidence: 99%

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Wood-Sourced Polymers as Support for Catalysis by Group 10 Transition Metals

et al. 2022

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Pd based on 2‐Aminopyrimidine and 1H‐benzo[d]imidazol‐2‐amine functionalizedFe₃O₄ nanoparticles as novel recyclable magnetic nanocatalysts for Ullmann coupling reaction

Jin

Dai

et al. 2020

Applied Organom Chemis

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In this study, Pd based on 2-Aminopyrimidine and 1H-benzo[d]imidazol-2-amine functionalized Fe 3 O 4 magnetic nanoparticles [(Pd-APM-PSi-Fe 3 O 4) and (Pd-BIA-PSi-Fe 3 O 4)] was designed and used for the synthesis of di aryl ether by Ulmann cross-coupling reactions. Ulmann reaction performed with mixing of the arylhalides and phenol derivatives in DMF solvent. The prepared catalysts were characterized with various analytical techniques such as FT-IR, XRD, TGA, SEM, TEM, EDX, ICP and VSM. Pd-APM-PSi-Fe 3 O 4 and Pd-BIA-PSi-Fe 3 O 4 catalysts demonstrated good to excellent yields catalytic efficiency for Ulmann reactions in comparison with to commercial palladium catalysts. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup. Also, these novel magnetic nanocatalysts are superior to the industry standard Pd in every relevant aspect. They feature a way higher initial activity, a much more convenient separation, better recycling, and less contamination of the products. Last but not least, they can be very easily prepared from commercially available Fe 3 O 4 nanoparticles using standard laboratory equipment.

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Immobilization of copper nanoparticles on WO₃ with enhanced catalytic activity for the synthesis of 1,2,3‐triazoles

Amini

Hajipour

Akbari

et al. 2020

Applied Organom Chemis

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In this study, a heterogeneous catalyst based on copper nanoparticles immobilized on metal oxide, WO3, was fabricated using an impregnation method as an easy and straightforward nanoparticle synthesis strategy. The successful synthesis of the nanocatalyst was confirmed using various spectroscopic techniques such as X‐ray diffraction, scanning electron microscopy, energy dispersive X‐ray analysis, and transmission electron microscopy. The catalytic performance of the well‐characterized material was evaluated through the azide–alkyne cycloaddition reaction (click reaction) in the aqueous medium. To optimize reaction conditions, different reaction parameters such as nanocatalyst amount, reaction time, temperature, and solvents were studied. Experimental results showed that as‐prepared nanocatalyst (Cu/WO3) could act as an effective and reusable heterogeneous catalyst in water for the synthesis of 1,2,3‐triazoles in good‐to‐excellent yields. In addition, Cu/WO3 has some advantages such as simple preparation procedure, easy separation, and recyclability for three runs with no remarkable loss of catalytic activity, which is essential from a catalytic application point of view.

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Cellulose nanocrystals-Palladium, a novel recyclable catalyst for coupling reaction

Cited by 7 publications

References 17 publications

Wood-Sourced Polymers as Support for Catalysis by Group 10 Transition Metals

Wood-Sourced Polymers as Support for Catalysis by Group 10 Transition Metals

Pd based on 2‐Aminopyrimidine and 1H‐benzo[d]imidazol‐2‐amine functionalizedFe₃O₄ nanoparticles as novel recyclable magnetic nanocatalysts for Ullmann coupling reaction

Immobilization of copper nanoparticles on WO₃ with enhanced catalytic activity for the synthesis of 1,2,3‐triazoles

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Cellulose nanocrystals-Palladium, a novel recyclable catalyst for coupling reaction

Cited by 7 publications

References 17 publications

Wood-Sourced Polymers as Support for Catalysis by Group 10 Transition Metals

Wood-Sourced Polymers as Support for Catalysis by Group 10 Transition Metals

Pd based on 2‐Aminopyrimidine and 1H‐benzo[d]imidazol‐2‐amine functionalizedFe3O4 nanoparticles as novel recyclable magnetic nanocatalysts for Ullmann coupling reaction

Immobilization of copper nanoparticles on WO3 with enhanced catalytic activity for the synthesis of 1,2,3‐triazoles

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Pd based on 2‐Aminopyrimidine and 1H‐benzo[d]imidazol‐2‐amine functionalizedFe₃O₄ nanoparticles as novel recyclable magnetic nanocatalysts for Ullmann coupling reaction

Immobilization of copper nanoparticles on WO₃ with enhanced catalytic activity for the synthesis of 1,2,3‐triazoles