A recyclable self-supported nanoporous PdCu heterogeneous catalyst for aqueous Suzuki–Miyaura cross-coupling

Du, Jialei; Xiang, Daili; Chen, Jie; Xia, Hengchuan; Wang, Leichen; Liu, Fushan; Zhao, Yiwei; Zhang, Yuanyuan; Xu, Caixia; Wang, Bin

doi:10.1039/d1cc04281e

Cited by 6 publications

(3 citation statements)

References 49 publications

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“…The palladium (Pd)-catalyzed Suzuki–Miyaura cross-coupling reaction is a general and efficient strategy for the construction of carbon–carbon (C–C) bonds in agrochemicals, pharmaceutical intermediates, and precursors for materials. − Motivated by sustainable and green chemistry, various novel heterogeneous Pd nanoparticle (NP) catalysts have been developed in recent years over conventional homogeneous Pd-based organometallic catalysts. − Generally, metal nanoparticles (MNPs) are immobilized on different supports, and their performance in catalysis depends mainly on the physical surface properties, size effects, and metal–support interactions . In the typical approach to prepare supported Pd catalysts, NPs are obtained by the reduction of dissolved Pd precursors in a solvent, and they are subsequently distributed onto the desired support .…”

Section: Introductionmentioning

confidence: 99%

Micelle-Derived Palladium Nanoparticles for Suzuki–Miyaura Coupling Reactions in Water at Room Temperature

Zhang

Yang

et al. 2023

ACS Appl. Nano Mater.

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Despite the wide utility of colloidal palladium (Pd) nanoparticle (NP)-catalyzed Suzuki−Miyaura cross-coupling reactions in laboratory and industrial synthesis, the easy construction of colloidal Pd NPs and the detailed role of surfactants remain the focus of attention. Here, we present a simple and sustainable strategy to construct a nanoreactor by connecting micelles with Pd NPs. The strategy enables us to employ a pH-induced morphological transition of sugar-based surfactant aggregates, such as worm-like, spherical, and tubular micelles, to investigate the solubilization of organic substrates. Pd NPs are mainly synthesized by the reduction of phenylboronic acid, further stabilized by the sugar-based surfactant micelles. A kinetic model is established, and the apparent activation energy of this reaction in aqueous micellar solutions is determined to be 46.7 kJ/mol. Notably, the recycled aqueous reaction mixture containing the micelles and Pd NPs can be reused.

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Section: Introductionmentioning

confidence: 99%

Micelle-Derived Palladium Nanoparticles for Suzuki–Miyaura Coupling Reactions in Water at Room Temperature

Zhang

Yang

et al. 2023

ACS Appl. Nano Mater.

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“…The cross-coupling reaction is one of the most powerful and general tools for the production of C–C bonds. − Among them, palladium (Pd)-catalyzed Suzuki–Miyaura cross-coupling plays a prominent role in the straightforward and efficient synthesis of binary compounds from the organoboron reagents with aryl halides and has been widely utilized in the production of agrochemicals, polymers, pharmaceutical intermediates, and fine chemical industries. − Usually, the reaction is catalyzed by soluble palladium complexes with different ligands in organics or aqueous media, and most of them are homogeneous, which presents difficulties in separating the catalyst from the final product. As is well known, the recovery and reusability of catalysts are of great significance for sustainable chemical processes.…”

Section: Resultsmentioning

confidence: 99%

CO₂-Triggered Hierarchical-Pore UiO-66-Based Pickering Emulsions for Efficient and Recyclable Suzuki–Miyaura Cross-Coupling in Biphasic Systems

Pei,

Song

2023

Langmuir

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Hierarchical-pore metal−organic frameworks (H-MOFs) are considered to be emerging stabilizers for Pickering emulsion formation because of their hierarchically arranged pores, tailorable structures, and ultrahigh surface areas. However, stimulus-triggered Pickering emulsions built by H-MOFs have been seldom presented to date despite their great significance in diverse applications. Herein, by grafting Pd(OAc) 2 on the hierarchical-pore zirconium MOF UiO-66, namely, H-UiO-66, with the aid of 1alkyl-3-methylimidazolium 2-cyanopyrrolide salts ([C n MIM][2-CN-Pyr], n = 4, 6, and 8), a series of Pd(OAc) 2 -[C n MIM][2-CN-Pyr]@H-UiO-66 have been developed and utilized as emulsifiers for constructing CO 2 -switching Pickering emulsions. It was found that Pd(OAc) 2 -[C n MIM][2-CN-Pyr]@H-UiO-66 was able to stabilize the n-hexane− water mixture to form a Pickering emulsion even at an amount of 0.5 wt %. Upon alternate addition of CO 2 and N 2 at normal pressure, Pickering emulsions could be smartly converted between demulsification and re-emulsification. Through combining varieties of spectroscopic techniques, the mechanism of the switchable phase transformation lay in the acid−base reaction of ionic liquids with CO 2 on H-UiO-66 and the creation of more hydrophilic salts, which reduced the wettability of the emulsifier and destabilized the emulsion. As an example of application, the stimulus-triggered Pickering emulsion was employed as a palladium-catalyzed Suzuki−Miyaura cross-coupling microreactor to achieve the combination of chemical reactions, isolation of products, and recovery of catalysts.

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“…Their unique structure sets them apart from their bulk counterparts and provides abundant active sites for potential chemical reactions, making them desirable for catalytic applications. ,− Additionally, nanoporous metals offer tunable pore sizes and distributions, allowing for customization of mechanical strength, permeability, and diffusion. They also display interesting electrical and thermal conductivities, enabling efficient electron and heat transport.…”

Section: Introductionmentioning

confidence: 99%

3D Nanoporous Metallic Networks for SERS-Based Detection of Water Contaminants

Hamode,

Ron,

Krause

et al. 2024

ACS Appl. Nano Mater.

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We investigated the formation of nanoporous metallic networks through a physical vapor deposition (PVD) process. Utilizing transmission electron microscopy (TEM), we observe the early stages of growth, revealing the presence of large pores and pillars. Our findings highlight the significant influence of the electrostatic nature of the substrate on the metallic network growth, where repulsion and attraction mechanisms come into play during the deposition process. We extend the applicability of this method, demonstrating its versatility in fabricating macroscopic metallic networks composed of submicrometer building blocks on different substrates, among them an amber stone, in a one-step process. The resulting three-dimensional (3D) networks display distinctive nonlinear optical properties, including enhanced second harmonic generation (SHG) and surface-enhanced Raman scattering (SERS) responses. The latter is used to detect contamination in water down to 10 −8 M.

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A recyclable self-supported nanoporous PdCu heterogeneous catalyst for aqueous Suzuki–Miyaura cross-coupling

Abstract: Nanoporous PdCu (NP-PdCu) was prepared by the dealloying strategy from PdCuAl ternary alloy precursor and characterized systematically by SEM, TEM, XRD, and XPS. NP-PdCu was demonstrated to be a competent...

Cited by 6 publications

References 49 publications

Micelle-Derived Palladium Nanoparticles for Suzuki–Miyaura Coupling Reactions in Water at Room Temperature

Micelle-Derived Palladium Nanoparticles for Suzuki–Miyaura Coupling Reactions in Water at Room Temperature

CO₂-Triggered Hierarchical-Pore UiO-66-Based Pickering Emulsions for Efficient and Recyclable Suzuki–Miyaura Cross-Coupling in Biphasic Systems

3D Nanoporous Metallic Networks for SERS-Based Detection of Water Contaminants

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A recyclable self-supported nanoporous PdCu heterogeneous catalyst for aqueous Suzuki–Miyaura cross-coupling

Abstract: Nanoporous PdCu (NP-PdCu) was prepared by the dealloying strategy from PdCuAl ternary alloy precursor and characterized systematically by SEM, TEM, XRD, and XPS. NP-PdCu was demonstrated to be a competent...

Cited by 6 publications

References 49 publications

Micelle-Derived Palladium Nanoparticles for Suzuki–Miyaura Coupling Reactions in Water at Room Temperature

Micelle-Derived Palladium Nanoparticles for Suzuki–Miyaura Coupling Reactions in Water at Room Temperature

CO2-Triggered Hierarchical-Pore UiO-66-Based Pickering Emulsions for Efficient and Recyclable Suzuki–Miyaura Cross-Coupling in Biphasic Systems

3D Nanoporous Metallic Networks for SERS-Based Detection of Water Contaminants

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CO₂-Triggered Hierarchical-Pore UiO-66-Based Pickering Emulsions for Efficient and Recyclable Suzuki–Miyaura Cross-Coupling in Biphasic Systems