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Mesoporous Palladium N,N’-Bis(3-Allylsalicylidene)o-Phenylenediamine-Methyl Acrylate Resins as Heterogeneous Catalysts for the Heck Coupling Reaction

1
Depto. Físico-Química, Facultad de Ciencias Químicas, Universidad de Concepción, Edmundo Larenas 129, Concepción 4070371, Chile
2
Depto. de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, Sede Concepción, Autopista Concepción-Talcahuano 7100, Talcahuano 4300866, Chile
3
Millenium Nuclei on Catalytic Processes towards Sustainable Chemistry (CSC), Santiago 8340518, Chile
*
Author to whom correspondence should be addressed.
Materials 2019, 12(16), 2612; https://doi.org/10.3390/ma12162612
Received: 31 July 2019 / Revised: 12 August 2019 / Accepted: 14 August 2019 / Published: 16 August 2019
(This article belongs to the Special Issue Catalysts: Preparation, Catalytic Performance and Catalytic Reaction)
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Abstract

Palladium N,N’-bis(3-allylsalicylidene)o-phenylenediamine complex (PdAS) immobilized onto mesoporous polymeric methyl acrylate (MA) based resins (PdAS(x)-MA, x = 1, 2, 5, or 10 wt.%) were successfully prepared as heterogeneous catalysts for the Heck reaction. The catalysts were synthesized via radical suspension polymerization using PdAS as a metal chelate monomer, divinylbenzene and MA as co-monomers. The effect of the PdAS(x) content on the physicochemical properties of the resins is also reported. The catalysts were characterized by using a range of analytical techniques. The large surface area (>580 m2·g−1) and thermal stability (up to 250 °C) of the PdAS(x)-MA materials allows their application as catalysts in the C–C coupling reaction between iodobenzene and MA in the presence of trimethylamine at 120 °C using DMF as the solvent. The PdAS(10)-MA catalyst exhibited the highest catalytic performance with no significant catalytic loss being observed after five reuses, thereby indicating excellent catalyst stability in the reaction medium. View Full-Text
Keywords: porous polymer; metal chelate monomer; palladium coordinated polymer porous polymer; metal chelate monomer; palladium coordinated polymer
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Mella, C.; Torres, C.C.; Pecchi, G.; Campos, C.H. Mesoporous Palladium N,N’-Bis(3-Allylsalicylidene)o-Phenylenediamine-Methyl Acrylate Resins as Heterogeneous Catalysts for the Heck Coupling Reaction. Materials 2019, 12, 2612.

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