Dicarboxylic Acid‐Functionalized MCM‐41 with Embedded Palladium Nanoparticles as an Efficient Heterogeneous Catalyst for C–C Coupling Reactions

Amini, Mostafa M.; Mohammadkhani, Abolfazl; Bazgir, Ayoob

doi:10.1002/slct.201702622

Cited by 18 publications

(5 citation statements)

References 48 publications

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“…Several groups have proposed functionalized MCM-41 catalysed Suzuki-Miyaura coupling reactions. [71,79,96,97] Most of these catalytic systems presented high activity, excellent yields, low reaction time and mild reaction conditions as compared to previous reports involving homogeneous catalysts. The reported reaction tolerated a plethora of ring substituted aryl halides and boronic acids.…”

Section: Suzuki-miyaura Coupling Reactionmentioning

confidence: 91%

“…The plausible reaction mechanism is depicted in Figure 38. In a similar reaction, Bazgir et al [97] used palladium anchored on 1,2-dicarboxylic acid (DCA) functionalized MCM-41 (Pd@DCA-MCM-41) as hybrid catalyst and potassium carbonate as the base (Figure 36d). In a recent publication, Molaei et al [99] prepared biphenyls using Pd complex of DL-Pyroglutamic acid(PCA) linked MCM-41 [MCM-41@PCA/Pd] as hybrid catalyst (Figure 36e).…”

Section: Suzuki-miyaura Coupling Reactionmentioning

confidence: 99%

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Functionalized MCM‐41: Versatile Catalysts for Organic Transformations

et al. 2022

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Functionalized MCM-41 constitute a group of potent hybrid catalysts for organic reactions. Their pore size is large enough to house large substrate molecules, the large bulk of surface silanol groups helps in introduction of a variety of functionalities required for the catalytic action. The current review emphasizes the broad methodology for the synthesis of these catalysts, effect of functionalization on reaction parameters, stability, efficiency, selectivity, reusability along with limitations of these catalysts to organic transformations, from a green chemistry standpoint. Some selected mechanisms of catalytic action are also highlighted. The review demonstrates that surface functionalized MCM-41 constitute innovative and need based catalyst systems that catalyze reactions like Sonogashira, Suzuki, Heck, Friedel Craft reaction, Aldol and Knoevenagel condensation etc. Several other reactions like oxidation, reduction, dehydration, esterification, epoxidation, CÀ S, CÀ N, CÀ O and SÀ S coupling as well as multicomponent synthesis of bioactive heterocycles have also been reported. It is hoped that this review will improve the understanding of scientific community on how these versatile catalysts operate and will provide opportunities to further enhance their utility for chemical industry.

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Section: Suzuki-miyaura Coupling Reactionmentioning

confidence: 91%

Section: Suzuki-miyaura Coupling Reactionmentioning

confidence: 99%

Functionalized MCM‐41: Versatile Catalysts for Organic Transformations

et al. 2022

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“…[139] Bazgir et al synthesized a novel PdNPs immobilized on 1,2dicarboxylic acid-functionalized (DCA) MCM-41 [Pd@DCA-MCM]. The catalyst displayed high catalytic activity towards the Hiyama coupling reaction of aryl halides and triethoxyphenylsilane in 1 : 1 H 2 0À EtOH solvent to corresponding biaryls in excellent yields after 3 h. [140] Recently, novel nickel NPs stabilized with triazole-functionalized SiO 2 @Fe 3 O 4 (TFÀ SiO 2 @Fe 3 O 4 À Ni) were designed by Abolfathi and Hajipour. They investigated their catalytic activity for the Hiyama crosscoupling of phenyltrimethoxysilane with aryl halides to biaryls in a water/ethanol solvent mixture.…”

Section: Mp (°C)mentioning

confidence: 99%

Solid‐Supported Catalysts for Organic Functional Group Transformations

et al. 2023

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Design of solid‐supported metal catalysts (SSMCs) has made an increasingly important contribution to heterogeneous catalysis in terms of fundamental understanding and technological applications. For instance, industrial use of supported catalysts for oxidation, reduction, and C−C bond formation reactions is highly prevalent. The reason behind this is that such catalysts are economical, have high thermal stability, dispersion, high exposed surface area, and above all, high reusability (up to multiple subsequent cycles). Such characteristics make supported catalysts ideal for green synthesis. However, unlike homogeneous catalysis, heterogeneous catalysis is widely applied in crude oil refining, the pharmaceutical industry, water purification, natural product synthesis, and environmental catalysis. Carbon‐carbon bond formation reactions are frequently used in the organic synthesis using SSMCs. SSMCs are attractive to synthetic chemists due to their easy recovery and excellent stability compared to unsupported metal catalysts. However, the major drawback of SSMCs is related to metal sintering at elevated temperatures caused by weak interactions between the metal and solid support in SSMCs. This review highlights major advancements in SSMCs. Three commonly reported solid supports for metal catalysts, such metal oxides, carbonaceous materials, and polymeric compounds, are discussed. Moreover, a series of thermo‐ and photocatalyzed reactions, such as hydrogenation, carbon‐carbon bond formation, oxidation reactions and multicomponent reactions and the effect of variable supports towards activity and selectivity are demonstrated.

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“…The Bazgir group fabricated a catalyst by reacting MCM-41 with 2-(trimethoxysilyl)ethane-1-thiol and then treated the product with maleic anhydride, followed by hydrolysis. [51] Finally, a reaction with Pd(OAc) 2 in acetonitrile gave the catalyst (6.4 wt% Pd 0 -1-MCM-41). It was characterized by FT-IR, TGA, AAS, TEM, SEM, and EDS.…”

Section: Materials As Catalyst Supportsmentioning

confidence: 99%

Palladium Nanoparticles Supported on Porous Silica Materials as Heterogeneous Catalysts of C−C Coupling and Cross‐Coupling Reactions

Mastalir

Molnár

2023

ChemCatChem

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Noble metal nanoparticles supported on porous silica materials represent an important class of heterogeneous catalysts. Various synthesis strategies have been developed, including the application of ligand‐assisted metal precursors, multistep synthesis procedures, post‐synthetic modifications, and magnetic mesoporous silica particles. Emphasis has been laid on the introduction of green procedures, based on the utilization of environmentally friendly solvents, efficient stabilizing agents, non‐toxic reagents, and mild reaction conditions. Palladium nanoparticles have long been recognized as the most efficient catalysts in a wide range of organic transformations, including the Heck, Suzuki, Stille, and Sonogashira reactions. Although these transformations have been extensively investigated in homogeneous catalytic systems, the application of heterogeneous catalysts, including silica‐supported Pd0 nanoparticles, has gained in increasing importance. The aim of this review is to provide an outlook on the current research progress achieved on the development of novel synthetic procedures, affording highly dispersed Pd0 nanoparticles immobilized on porous silica materials, which proved to be efficient and recyclable catalysts in C–C coupling and cross‐coupling reactions.

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Dicarboxylic Acid‐Functionalized MCM‐41 with Embedded Palladium Nanoparticles as an Efficient Heterogeneous Catalyst for C–C Coupling Reactions

Cited by 18 publications

References 48 publications

Functionalized MCM‐41: Versatile Catalysts for Organic Transformations

Functionalized MCM‐41: Versatile Catalysts for Organic Transformations

Solid‐Supported Catalysts for Organic Functional Group Transformations

Palladium Nanoparticles Supported on Porous Silica Materials as Heterogeneous Catalysts of C−C Coupling and Cross‐Coupling Reactions

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