Recent Progress in Application of Graphene Supported Metal Nanoparticles in C−C and C−X Coupling Reactions

Nasrollahzadeh, Mahmoud; Issaabadi, Zahra; Tohidi, Mohammad Mostafa; Sajadi, S. Mohammad

doi:10.1002/tcr.201700022

Cited by 96 publications

(42 citation statements)

References 208 publications

(128 reference statements)

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“…Composites based on graphene, as a novel nanomaterial, have attracted extensive attention in the field of catalysis due to their unique characteristics, such as a large surface area, chemical stability, strong hydrophobicity and easy modification . Recent calculations and experiments have shown that graphene‐supported palladium has excellent catalytic activity for carbon–carbon cross‐coupling reactions because graphene has a high binding energy with palladium and good charge storage performance .…”

Section: Graphenementioning

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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Section: Graphenementioning

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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“…The Sonogashira coupling between terminal alkynes and aromatic halides has been studied using different palladium species, mainly PdNPs, immobilized on carbonaceous materials such as carbon nanotubes, graphene-derived materials [51] and carbon itself. In general, good activity and recyclability have been observed when employing supported PdNPs, especially when activated electrophiles, such as aryl iodides and bromides are coupled with aromatic terminal alkynes.…”

Section: Carbon-based Material-supported Palladium Catalystsmentioning

confidence: 99%

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

et al. 2018

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Abstract:The Sonogashira cross-coupling reaction is the most frequently employed synthetic procedure for the preparation of arylated alkynes, which are important conjugated compounds with multiple applications. Despite of their rather high price, this reaction is usually catalyzed by palladium species, making the recovery and reuse of the catalyst an interesting topic, mainly for industrial purposes. Easy recycle can be achieved anchoring the palladium catalyst to a separable support. This review shows recent developments in the use of palladium species anchored to different solid supports as recoverable catalysts for Sonogashira cross-coupling reactions.

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“…In addition, practical limitations, such as catalyst operation, reusability, and isolation of the catalyst from products, hinder the advantages of homogeneous Pd catalysts in large-scale industrial processes. By contrast, a heterogeneous Pd catalyst could obviate these limitations and open up a valuable alternative technology in such processes [13][14][15][16][17]. In recent years, palladium nanoparticles (NPs) supported by various substrates, such as active carbon materials [18,19], silica [20][21][22], polymers [23,24], inorganic mineral [25,26], metal oxides [27][28][29], and covalent organic frameworks (COFs) [30,31] have been designed and applied for the Suzuki-Miyaura reaction.…”

Section: Introductionmentioning

confidence: 99%

Pd–Co Nanoparticles Supported on Calcined Mg–Fe Hydrotalcites for the Suzuki–Miyaura Reaction in Water with High Turnover Numbers

et al. 2019

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We reveal the Suzuki-Miyaura reaction catalyzed by a Pd-Co nanocatalyst supported by Mg-Fe-CHT (calcined hydrotalcites). A variety of boronic acids and aryl halides were transformed into functionalized biphenyls in excellent yields using water as a solvent. The reaction could proceed under mild conditions with a simple operation and high turnover numbers. The excellent catalytic activities are reasonably attributed to the Co-doping, which forms a Pd-Co alloy on the surface of CHT.The preparation of the Pd/Co-Mg-Fe-CHT catalyst is shown in Scheme 1 via a co-precipitation method. Using the analogous operation, we also prepared Mg-Fe-CHT and Co-Mg-Fe-CHT. In our initial evaluation of the Suzuki-Miyaura coupling condition, iodobenzene and phenylboronic acid were used as model substrates with two equivalents of base and 10 mg Pd or Co nanoparticles (NPs) prepared by various methods (Supplementary Materials) [39][40][41]. We found that the Pd-NPs supported by Mg-Fe-CHT could promote the coupling reaction with 93% yield (Table 1, Entry 1). With a view to recycle the catalyst, we prepared Pd-doped Co-NPs supported by Mg-Fe-CHT. The inductively coupled plasma (ICP) analysis showed that the Pd and Co content in calcined hydrotalcite is 0.49 wt % and 0.67 wt %, respectively.

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Recent Progress in Application of Graphene Supported Metal Nanoparticles in C−C and C−X Coupling Reactions

Cited by 96 publications

References 208 publications

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

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

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

Pd–Co Nanoparticles Supported on Calcined Mg–Fe Hydrotalcites for the Suzuki–Miyaura Reaction in Water with High Turnover Numbers

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