Palladium complex supported on the surface of magnetic Fe3O4 nanoparticles: an ecofriendly catalyst for carbonylative Suzuki-coupling reactions† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3ra06533b
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SUBMITTER: Jiang S
PROVIDER: S-EPMC10690082 | biostudies-literature | 2023 Dec
REPOSITORIES: biostudies-literature
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Project description:The application of metal-organic frameworks (MOFs) has attracted increasing attention in organic synthesis. The modification of MOFs can efficiently tailor the structure and improve the property for meeting ongoing demand in various applications, such as the alteration of gas adsorption and separation, catalytic activity, stability, and sustainability or reusability. In this study, carboxyethylsilanetriol (CEST) disodium salt was used as a dual-functional ligand for modified Al-MIL-53 to fabricate CEST-functionalized Al-MIL-53 samples through a hydrothermal reaction of aluminum nitrate, terephthalic acid, and CEST disodium salt by varying the molar ratio of CEST to terephthalic acid and keeping a constant molar ratio of Al3+/-COOH of 1:1. The structure, composition, morphology, pore feature, and stability were characterized by XRD, different spectroscopies, electron microscopy, N2 physisorption, and thermogravimetric analysis. With increasing CEST content, CEST-Al-MIL-53 still preserves an Al-MIL-53-like structure, but the microstructure changed compared with pure Al-MIL-53 due to the integration of CEST. Such a CEST-Al-MIL-53 was used as the support to load Pd particles and afford a catalyst Pd/CEST-Al-MIL-53 for Suzuki-Miyaura C-C cross-coupling reaction of aryl halides and phenylboronic acid under basic conditions. The resulting Pd/CEST-Al-MIL-53 showed a high catalytic activity compared with Pd/Al-MIL-53, due to the nanofibrous structure of silicon species-integrated CEST-Al-MIL-53. The nanofiber microstructure undergoes a remarkable transformation into intricate 3D cross-networks during catalytic reaction, which enables the leachable Pd particles to orientally redeposit and inlay into these networks as the monodisperse spheres and thereby effectively preventing Pd particles from aggregation and leaching, therefore demonstrating a high catalytic performance, long-term stability, and enhanced reusability. Obviously, the integration of CEST into MOFs can effectively prevent the leaching of active Pd species and ensure the re-deposition during catalysis. Moreover, catalytic performance strongly depended on catalyst dosage, temperature, time, solvent, and the type of the substituted group on benzene ring. This work further extends the catalytic application of hybrid metal-organic frameworks.
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Project description:An efficient Suzuki cross-coupling reaction under continuous flow conditions was developed utilizing an immobilized solid supported catalyst consisting of bimetallic nickel-palladium nanoparticles (Ni-Pd/MWCNTs). In this process, the reactants can be continuously pumped into a catalyst bed at a high flow rate of 0.6 mL/min and the temperature of 130 °C while the Suzuki products are recovered in high steady-state yields for prolonged continuous processing. The catalyst was prepared by mechanical shaking of the appropriate nickel and palladium salts using ball-mill energy without the requirement of any solvent or reducing agent. This straightforward, facile, and simple method allows for bulk production of Ni-Pd/MWCNTs nanoparticles with a small particle size ideal for application in continuous flow cross-coupling catalysis. The as-prepared catalyst mostly contains nickel (7.9%) with a very small amount of palladium (0.81%) according to ICP-OES analysis. This remarkable immobilized catalyst can be used several times for different Suzuki reactions with a minimum loss of reactivity and no detectable leaching of the metal nanoparticles. Notably, by modifying the groups on both aryl halides and phenylboronic acids, the method provides access to a diverse array of the Suzuki products in flow with high steady-state yield, making it suitable for applications in industrial and pharmaceutical scales. Moreover, several spectroscopic techniques were employed to identify the structure and composition of the as-prepared Ni-Pd/MWCNTs nanoparticles before and after the reaction in flow such as transmission electron microscopy (TEM), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), thermogravimetric analysis (TGA), BET surface area (physisorption), and FTIR spectroscopy.
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