Palladium Stabilized by Amino-Vinyl Silica Functionalized Magnetic Carbon Nanotube: Application in Suzuki–Miyaura and Heck–Mizoroki Coupling Reactions

Khalili, Dariush; Banazadeh, Ali Reza; Etemadi‐Davan, Elham

doi:10.1007/s10562-017-2150-1

Cited by 33 publications

(27 citation statements)

References 74 publications

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“…In the case of Suzuki reactions in pure water, results were comparable or even better than those obtained with commercial Pd/C [23] or other supported Pd-based catalysts. [11a,13a,15a, [24][25][26][27][28][29][30][31][32] Both catalysts were recovered after centrifugation and reused in up to five cycles without loss in catalytic activity. Moreover, the catalytic loading was also scaled down to 0.01 and 0.007 mol% for MWCNT-imi-Pd 3 and CNH-imi-Pd 5, respectively, still giving high TON values.…”

Section: Discussionmentioning

confidence: 99%

Templating effect of carbon nanoforms on highly cross‐linked imidazolium network: Catalytic activity of the resulting hybrids with Pd nanoparticles

Campisciano

Calabrese

Liotta

et al. 2019

Applied Organom Chemis

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Two different carbon nanoforms (CNFs), namely multi‐walled carbon nanotubes (MWCNTs) and carbon nanohorns (CNHs), have been chosen as support for the direct polymerization of a bis‐vinylimidazolium salt. Transmission electron microscopy analyses revealed a templating effect of the CNFs on the growth of the polymeric network, which perfectly covers their whole surfaces creating a cylindrical or spherical coating for MWCNTs and CNHs, respectively. Subsequently, the CNFs‐polyimidazolium have been used as stabilizers for Pd nanoparticles (Pd NPs), and the obtained materials have been characterized by means of analytical and spectroscopic techniques and then employed as easily recoverable and recyclable catalysts for Suzuki and Heck reactions. Quantitative conversions have been obtained in almost all the explored reactions, even employing low loading of catalyst (down to 0.007 mol%). Suzuki reactions were carried out in pure water under aerobic conditions. Both materials showed excellent activity and recyclability for the investigated C‐C coupling reactions, with the CNHs‐based material resulting slightly more active than the MWCNTs‐based one due to a higher superficial exposure of Pd NPs.

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Section: Discussionmentioning

confidence: 99%

Templating effect of carbon nanoforms on highly cross‐linked imidazolium network: Catalytic activity of the resulting hybrids with Pd nanoparticles

Campisciano

Calabrese

Liotta

et al. 2019

Applied Organom Chemis

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“…In 2017, Khalili and coworkers reported the preparation of a Pd catalyst based on amino‐vinyl silica‐functionalized magnetic CNTs using the strategy shown in Scheme . The functionalized SiO 2 contributed to the stability of Pd NPs and was also responsible for the reduction of Pd 2+ without adding external reducing agents.…”

Section: Carbon Nanotubesmentioning

confidence: 99%

“…In 2017, Khalili and coworkers reported the preparation of a Pd catalyst based on amino-vinyl silicafunctionalized magnetic CNTs using the strategy shown in Scheme 7. [85] The functionalized SiO 2 contributed to the stability of Pd NPs and was also responsible for the reduction of Pd 2+ without adding external reducing agents. The catalysts showed high activity and stability toward Suzuki reactions of aryl electrophiles under low Pd loading conditions and could also be recovered easily by using an external magnet.…”

Section: Pd Nps Immobilized On Functionalized Cnts (F-cnts)mentioning

confidence: 99%

Carbon‐Based Material‐Supported Palladium Nanocatalysts in Coupling Reactions: Discussion on their Stability and Heterogeneity

Zhao

Cao

2020

Applied Organom Chemis

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Scientific interest in carbon‐based materials (CBMs) has grown dramatically over the past few decades. Due to a variety of atomic orbital hybrid forms (sp, sp2 and sp3 hybridization), carbon can form a variety of materials with diverse structures and characteristics. CBMs used as efficient catalyst supports show extensive promise in organic reactions, which is attributed to their structural similarity with organics, large specific surface area, chemical stability, and photocatalytic properties. This review presents the synthesis of CBM‐supported palladium nanocatalysts based on impregnation, template methods, etc. The CBMs include activated carbon (AC), graphene, carbon nanotubes (CNTs), and their functionalized products, as supports for improving the activity and recyclability of simple Pd nanocatalysts. After surveying the literature where these catalysts have been utilized for carbon–carbon coupling reactions, there is a particular emphasis on Suzuki, Heck, and Sonogashira reactions. The catalytic mechanism of these Pd nanocatalysts (surface heterogeneous catalysis or homogeneous catalysis caused by Pd leaching) is discussed in detail, especially the effect of Pd leaching on the stability of the catalyst.

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“…Pd NPs supported on amino-vinyl silica functionalized magnetic CNTs (CNT@Fe 3 O 4 @SiO 2 -Pd) have been reported by Khalili and co-workers. [90] For the preparation of this material, CNTs were treated with HNO 3 under MW heating at 160°C for 30 min after isolation were treated with FeCl 2 ·4H 2 O and out with aryl iodides, bromides and chlorides with the same Pd loading, K 2 CO 3 as base, TBAB as additive, in DMF at 130°C.…”

Section: Palladium-supported On Carbon Nanotubesmentioning

confidence: 99%

Carbon‐Derived Supports for Palladium Nanoparticles as Catalysts for Carbon‐Carbon Bonds Formation

Naghshbandi

Nájera

2019

ChemCatChem

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The review considers the variety allotropes of carbon to be used as supports for palladium and investigation of the resulting catalysts for carbon‐carbon forming reactions with focus on the catalyst recovery and effect of the solvent, base and catalyst loading in the efficiency of reactions. Specially, carbon nanotubes, C60 and graphene allowed the covalent functionalization with different ligands for palladium facilitating a lower leaching. Magnetic iron nanoparticles can be easily covered by charcoal, graphene oxide and carbon quantum dots facilitating the recovery of the supported catalyst. These heterogeneous catalysts are able to activate even aryl chlorides in cross‐coupling reactions such as Suzuki‐Miyaura, Mizoroki‐Heck and Sonogashira‐Hagihara in organic but also in aqueous media. All these features favoured the applicability of the materials for industrial processes.

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Palladium Stabilized by Amino-Vinyl Silica Functionalized Magnetic Carbon Nanotube: Application in Suzuki–Miyaura and Heck–Mizoroki Coupling Reactions

Cited by 33 publications

References 74 publications

Templating effect of carbon nanoforms on highly cross‐linked imidazolium network: Catalytic activity of the resulting hybrids with Pd nanoparticles

Templating effect of carbon nanoforms on highly cross‐linked imidazolium network: Catalytic activity of the resulting hybrids with Pd nanoparticles

Carbon‐Based Material‐Supported Palladium Nanocatalysts in Coupling Reactions: Discussion on their Stability and Heterogeneity

Carbon‐Derived Supports for Palladium Nanoparticles as Catalysts for Carbon‐Carbon Bonds Formation

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