Preparation and characterization of new palladium complex immobilized on (chitosan)/PoPD biopolymer and its catalytic application in Suzuki cross‐coupling reaction

Seyedi, Neda; Zahedifar, Mahboobeh

doi:10.1002/aoc.6487

Cited by 7 publications

(3 citation statements)

References 72 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2022, Seyedi et al described the preparation of a palladium catalyst deposited on a poly(o-phenylenediamine)-grafted chitosan in a two-step procedure: first, an aqueous solution of chitosan was treated with o-phenylenediamine for 1 h at room temperature in the presence of sulfuric acid, in order to allow the in situ polymerization of o-phenylenediamine, giving the grafted biopolymer (indicated as CS-PoPD); the resulting CS-PoPD was then added to a solution of PdCl 2 in methanol, and the resulting suspension was stirred for 24 h at room temperature to give the final supported catalyst (named CS-PoPD-Pd) [110]. In particular, the immobilization of palladium occurred in the form of Pd(II) complexes, as confirmed by the XRD pattern: no new diffraction peaks appeared after the treatment of the CS-PoPD support with PdCl 2 ; moreover, SEM images showed that the o-phenylenediamine polymerization led to a flake-like structure.…”

Section: Cross-coupling Reactions Promoted By Palladium Catalysts Sup...mentioning

confidence: 99%

See 1 more Smart Citation

Palladium Supported on Bioinspired Materials as Catalysts for C–C Coupling Reactions

2023

View full text Add to dashboard Cite

In recent years, the immobilization of palladium nanoparticles on solid supports to prepare active and stable catalytic systems has been deeply investigated. Compared to inorganic materials, naturally occurring organic solids are inexpensive, available and abundant. Moreover, the surface of these solids is fully covered by chelating groups which can stabilize the metal nanoparticles. In the present review, we have focused our attention on natural biomaterials-supported metal catalysts applied to the formation of C–C bonds by Mizoroki–Heck, Suzuki–Miyaura and Sonogashira reactions. A systematic approach based on the nature of the organic matrix will be followed: (i) metal catalysts supported on cellulose; (ii) metal catalysts supported on starch; (iii) metal catalysts supported on pectin; (iv) metal catalysts supported on agarose; (v) metal catalysts supported on chitosan; (vi) metal catalysts supported on proteins and enzymes. We will emphasize the effective heterogeneity and recyclability of each catalyst, specifying which studies were carried out to evaluate these aspects.

show abstract

Section: Cross-coupling Reactions Promoted By Palladium Catalysts Sup...mentioning

confidence: 99%

“…Scheme 35. Suzuki-Miyaura coupling of aryl halides with phenyl boronic acid promoted by a palladium catalyst deposited on a poly(o-phenylenediamine)-grafted chitosan (CS-PoPD-Pd), reported in 2022 by Seyedi et al [110].…”

Section: Cross-coupling Reactions Promoted By Palladium Catalysts Sup...mentioning

confidence: 99%

Palladium Supported on Bioinspired Materials as Catalysts for C–C Coupling Reactions

2023

View full text Add to dashboard Cite

show abstract

“…Therefore, to obtain a good yield of the desired cross-coupled product, the reaction was studied by varying different reaction parameters. Literature reports suggest that the solvent system plays a vital role in the SMCC reaction. ,, Hence using the same amount of substrate, catalyst, and base, the reaction was performed in different organic solvents at room temperature. The solvent optimization graph depicted in Figure S7 suggested that CH 3 OH was more suitable in comparison to other solvents like EtOH, CH 3 CN, and isopropanol for this particular reaction under these conditions.…”

Section: Catalytic Studymentioning

confidence: 99%

Low-Palladium-Content Iron(III) Nanocatalyst Supported on Zeolite-NaY for C–Cl Bond Activation

Bora,

Hazarika,

Gour

et al. 2023

ACS Appl. Nano Mater.

View full text Add to dashboard Cite

A heterogeneous nanocatalyst comprising palladium (Pd/PdO) and iron(III) oxide (Fe 2 O 3 ) in the dimension of 1−4 nm was synthesized using sodium-exchanged zeolite-Y or zeolite-NaY [a type of faujasite (FAU) zeolite having an aluminosilicate framework with a general formula of (Na 2 ) 3.5 [Al 7 Si 17 O 48 ]•32H 2 O] as a support matrix. The catalyst was investigated as a true heterogeneous catalyst for activation of the robust C−Cl bond of aryl chlorides in the Suzuki−Miyaura cross-coupling (SMCC) reaction. The catalyst with very low Pd loading (0.0037 mol %) exhibited high reactivity in the SMCC reaction with various derivatives of aryl chlorides (Ar−Cl). Biaryl products were obtained with up to a 92% yield, high selectivity, and a good turnover number with this Pd/PdO−Fe 2 O 3 -Y catalyst. The catalyst exhibited good thermal stability and was highly recyclable. The reaction was found to be reliant on various parameters such as solvent system, temperature, time, and catalyst amount. A small aliquot of water (H 2 O) mixed with methanol (CH 3 OH) dramatically brought a substantial improvement in the product yield of the desired biaryl product. The role of zeolite-NaY was also investigated by comparing the results with various other synthesized catalysts. Different experimental studies indicated that the surface hydroxyl (−OH) groups of zeolite-NaY, modification of basic sites, and the ability to influence the reduction temperature of iron (Fe) and palladium (Pd) influenced the catalytic performance of the synthesized catalyst. The impact of Fe on the electronic structure and reactivity of Pd was analyzed through a density functional theory calculation. This study provided strong evidence for creation of a negative (−ve) charge on Pd with an increasing amount of Fe content and thereby favored the in situ transformation of Pd(II) to Pd(0) as required in the activation of the C−Cl bond.

show abstract

Chitosan‐Ethylenediaminetetraacetic acid‐palladium composite for the Suzuki–Miyaura reaction

Khomthawee

Nilada

Homchuen

et al. 2022

Applied Organom Chemis

View full text Add to dashboard Cite

Palladium catalyst supported on chitosan‐EDTA composite, CS‐EDTA‐Pd, was prepared by a simple dissolution method. The chitosan and EDTA (1:1.5 by wt.) were dissolved in dilute acetic acid, then formed the beads, which were used to adsorb palladium(II) and finally reduced to palladium(0) by refluxing in ethanol. The as‐prepared CS‐EDTA‐Pd was characterized by Fourier transform infrared (FT‐IR) spectroscopy, scanning electron microscopy (SEM), energy dispersive X‐ray spectrometry (EDX), and X‐ray photoelectron spectroscopy (XPS). Then catalytic activities of the CS‐EDTA‐Pd catalyst were tested in the synthesis of biaryls from aryl halides and phenylboronic acid using the Suzuki–Miyaura cross‐coupling reaction. The results have shown that the CS‐EDTA‐Pd was successfully applied as a catalyst for the Suzuki–Miyaura to couple aryl iodide and aryl bromide substrates under mild reaction conditions using ethanol as solvent and potassium carbonate as a base. The reactions at 80°C for 2 h under a normal atmosphere results in biaryls at good to excellent yields (>90%). This catalyst is inexpensive, simple to prepare, easy to separate from the reaction by filtration, and can be reused for five consecutive runs with a slight loss of product yields.

show abstract

Preparation and characterization of new palladium complex immobilized on (chitosan)/PoPD biopolymer and its catalytic application in Suzuki cross‐coupling reaction

Cited by 7 publications

References 72 publications

Palladium Supported on Bioinspired Materials as Catalysts for C–C Coupling Reactions

Palladium Supported on Bioinspired Materials as Catalysts for C–C Coupling Reactions

Low-Palladium-Content Iron(III) Nanocatalyst Supported on Zeolite-NaY for C–Cl Bond Activation

Chitosan‐Ethylenediaminetetraacetic acid‐palladium composite for the Suzuki–Miyaura reaction

Contact Info

Product

Resources

About