Dataset Information

Synthesis of nano magnetic supported NHC-palladium and investigation of its applications as a catalyst in the Mizoroki-Heck cross-coupling reaction in H₂O.

ABSTRACT: The unique properties of N-heterocyclic carbenes (NHCs) as an effective ligand for palladium catalytic centers have recently found much attention. In this work, Fe₃O₄ nanoparticle supported palladium(II)-N-heterocyclic carbene catalyst was successfully designed, synthesized and characterized by various methods. The activity of the catalyst was evaluated in the Mizoroki-Heck cross-coupling reaction in which the desired products were obtained in high yield in H₂O as a green solvent. The reaction was carried out in short reaction times using low amounts of the catalyst. Moreover, the catalyst was easily separated from the reaction media and reused for 5 cycles.

SUBMITTER: Ghavidel Kalishomi R

PROVIDER: S-EPMC7511807 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Synthesis of nano magnetic supported NHC-palladium and investigation of its applications as a catalyst in the Mizoroki-Heck cross-coupling reaction in H2O.

Ghavidel Kalishomi Razieh R Rostamizadeh Shahnaz S Nouri Fatemeh F Khazaei Ali A

Heliyon 20200923 9

The unique properties of N-heterocyclic carbenes (NHCs) as an effective ligand for palladium catalytic centers have recently found much attention. In this work, Fe3O4 nanoparticle supported palladium(II)-N-heterocyclic carbene catalyst was successfully designed, synthesized and characterized by various methods. The activity of the catalyst was evaluated in the Mizoroki-Heck cross-coupling reaction in which the desired products were obtained in high yield in H2O a ...[more]

PMID: 32995626

Similar Datasets

Project description:The formation of a C-C bond through Mizoroki-Heck cross-coupling reactions in water with efficient heterogeneous catalysts is a challenging task. In this current study, a highly reduced graphene oxide (HRG) immobilized palladium (Pd) nanoparticle based catalyst (HRG-Py-Pd) is used to catalyze Mizoroki-Heck cross-coupling reactions in water. During the preparation of the catalyst, amino pyrene is used as a smart functionalizing ligand, which offered chemically specific binding sites for the effective and homogeneous nucleation of Pd NPs on the surface of HRG, which significantly enhanced the physical stability and dispersibility of the resulting catalyst in an aqueous medium. Microscopic analysis of the catalyst revealed a uniform distribution of ultrafine Pd NPs on a solid support. The catalytic properties of HRG-Py-Pd are tested towards the Mizoroki-Heck cross-coupling reactions of various aryl halides with acrylic acid in an aqueous medium. Furthermore, the catalytic efficacy of HRG-Py-Pd is also compared with its non-functionalized counterparts such as HRG-Pd and pristine Pd NPs (Pd-NPs). Using the HRG-Py-Pd nanocatalyst, the highest conversion of 99% is achieved in the coupling reaction of 4-bromoanisol and acrylic acid in an aqueous solution in a relatively short period of time (3 h), with less quantity of catalyst (3 mg). Comparatively, pristine Pd NPs delivered lower conversion (∼92%) for the same reaction required a long reaction time and a large amount of catalyst (5.3 mg). Indeed, the conversion of the reaction further decreased to just 40% when 3 mg of Pd-NPs was used which was sufficient to produce 99% conversion in the case of HRG-Py-Pd. On the other hand, HRG-Pd did not deliver any conversion and was ineffective even after using a high amount of catalyst and a longer reaction time. The inability of the HRG-Pd to promote coupling reactions can be attributed to the agglomeration of Pd NPs which reduced the dispersion quality of the catalyst in water. Therefore, the high aqueous stability of HRG-Py-Pd due to smart functionalization can be utilized to perform other organic transformations in water which was otherwise not possible.

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

Synthesis of nano magnetic supported NHC-palladium and investigation of its applications as a catalyst in the Mizoroki-Heck cross-coupling reaction in H₂O.

Publications

Synthesis of nano magnetic supported NHC-palladium and investigation of its applications as a catalyst in the Mizoroki-Heck cross-coupling reaction in H<sub>2</sub>O.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets