Dataset Information

Efficient and Recyclable Solid-Supported Pd(II) Catalyst for Microwave-Assisted Suzuki Cross-Coupling in Aqueous Medium.

ABSTRACT: Solid-supported catalysts play efficient and crucial roles in organic synthesis. A solid-supported palladium(II) complex based on chitosan was synthesized and fully characterized using all possible tools (Fourier transform infrared spectroscopy, thermogravimetry analysis, differential scanning calorimetry, X-ray photoelectron spectroscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma atomic emission spectrometry, scanning electron microscopy, transmission electron microscopy, and Brunauer-Emmett-Teller analysis). The catalytic activity of the solid-phase catalyst in Suzuki cross-coupling reactions was evaluated in aqueous solvents under both conventional heating and microwave irradiation conditions. The recyclability and thermal stability of the prepared catalyst were also examined, and the catalyst was found to be active till five consecutive runs without a notable loss of activity under the microwave condition, with the turnover number and turnover frequency values reaching 19,019 and 114,114 h^-1, respectively.

SUBMITTER: Alazemi AM

PROVIDER: S-EPMC9404494 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Efficient and Recyclable Solid-Supported Pd(II) Catalyst for Microwave-Assisted Suzuki Cross-Coupling in Aqueous Medium.

Alazemi Abdulrahman M AM Dawood Kamal M KM Al-Matar Hamad M HM Tohamy Wael M WM

ACS omega 20220810 33

Solid-supported catalysts play efficient and crucial roles in organic synthesis. A solid-supported palladium(II) complex based on chitosan was synthesized and fully characterized using all possible tools (Fourier transform infrared spectroscopy, thermogravimetry analysis, differential scanning calorimetry, X-ray photoelectron spectroscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma atomic emission spectrometry, scanning electron microscopy, transmission electron microscopy, ...[more]

PMID: 36033663

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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.

Dataset Information

Efficient and Recyclable Solid-Supported Pd(II) Catalyst for Microwave-Assisted Suzuki Cross-Coupling in Aqueous Medium.

Publications

Efficient and Recyclable Solid-Supported Pd(II) Catalyst for Microwave-Assisted Suzuki Cross-Coupling in Aqueous Medium.

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