The effect of the hydrotalcite structure and nanoparticle size on the catalytic performance of supported palladium nanoparticle catalysts in Suzuki cross-coupling

Vaerenbergh, Beau Van; Vlieger, Kevin De; Claeys, Kyle; Vanhoutte, G.; Clercq, Jeriffa De; Vermeir, Pieter; Verberckmoes, An

doi:10.1016/j.apcata.2017.11.018

Cited by 27 publications

(14 citation statements)

References 67 publications

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“…Please note that knowing the contribution of the leached species is not straightforward since the Pd concentration in the solution varies with the conversion. This was observed by several authors, with a concentration varying by one order of magnitude between 50 and 100% conversion [44][45][46]. The values given in Table 2 have thus to be considered as orders of magnitude since the values of leached concentrations were not always associated with the conversions at which they have been measured.…”

Section: Solid Pre-catalysts Providing Active Species In Solutionmentioning

confidence: 78%

“…Using Pd nanoparticles supported on hydrotalcite for the coupling of iodobenzene with phenylboronic acid, Vaerenbergh et al [46] observed by ICP-AES a leaching of a few percent of Pd, with a concentration varying with the conversion (maximum of 2.6% Pd at 88% conversion). Redeposition of Pd on the surface occurred at full conversion.…”

Section: Solid Pre-catalysts Providing Active Species In Solutionmentioning

confidence: 99%

“…Measuring no Pd in solution is not a sufficient proof that Pd has not leached. It is known from several authors that the concentration of leached Pd varies with the conversion and/or the temperature [44][45][46]49]. Adsorption of the leached species on the solid at full conversion or when the temperature gets lower has to be kept in mind.…”

Section: Pd Trace-analysismentioning

confidence: 99%

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About Solid Phase vs. Liquid Phase in Suzuki-Miyaura Reaction

2019

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A critical review of conclusions about the putative heterogeneous mechanism in the Suzuki-Miyaura coupling by supported Pd solids is reported. In the first section, the turnover frequencies (TOF) of 20 well-established homogeneous catalysts are shown to be in the range 200 to 1,000,000,000 h − 1 . The evidences used to prove a heterogeneous mechanism are discussed and another interpretation is proposed, hypothesizing that only the leached species are responsible for the catalytic reaction, even at ppb levels. Considering more than 40 published catalytic systems for which liquid phase Pd content have been reported, activities have been computed based on leached Pd concentrations and are shown to be in the range TOF 150 to 70,000,000 h − 1 . Such values are compatible with those found for the well-established homogeneous catalysts which questions the validity of the conclusions raised by many papers about the heterogeneous (solid) nature of Suzuki-Miyaura catalysis. Last, a tentative methodology is proposed which involves the rational use of well-known tests (hot-filtration test, mercury test…) to help to discriminate between homogeneous and heterogeneous mechanisms.

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Section: Solid Pre-catalysts Providing Active Species In Solutionmentioning

confidence: 78%

Section: Solid Pre-catalysts Providing Active Species In Solutionmentioning

confidence: 99%

Section: Pd Trace-analysismentioning

confidence: 99%

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About Solid Phase vs. Liquid Phase in Suzuki-Miyaura Reaction

2019

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“…Heterogeneous catalysis has many advantages over homogeneous catalysis, such as easy recovery, recyclability, enhanced stability and lower degree of Pd contamination in the final products. Immobilization of Pd‐based catalysts to some supported solid materials such as carbon nanotubes, graphene, cellulose, chitosan/starch, agar/pectin composite, chitosan‐cellulose micro beads, agar, sporopollenin microcapsule, poly(4‐((pyridine‐2ylimino)methyl)benzene‐1,3‐diol), TiO 2 , montmorillonite K 10, zeolite Y, hydrotalcites, metal oxides, porous glass, carbon nanodiamond, metal–organic frameworks, and magnetic nanoparticles by physical adsorption or chemical bonding is a good method for solving the above problems. Although the rapid development of immobilization of Pd‐based catalysts has been achieved, in some cases, the catalytic activities are lower than those in their homogeneous counterparts, low recycle performance due to leaching of Pd from the support, the catalyst synthesis method is complicated, and high reaction temperature is always required.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and catalytic performance of palladium supported on pyridine‐based covalent organic polymer for Suzuki‐Miyaura reaction

Han

Zhao

et al. 2019

Applied Organom Chemis

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A bipyridine‐based covalent organic polymer (COP) was successfully synthesized by condensation of trimesoyl chloride (TMC) and 2,2′‐bipyridine‐5,5′‐diamine (Bpy) under ambient conditions. This material was modified by coordination of PdCl2 to COP framework, affording a hybrid material, Pd@TMC‐Bpy COP, which was applied as a highly efficient heterogeneous catalyst for Suzuki‐Miyaura reaction under ligand‐free conditions in ethyl lactate. The catalyst could be reused for five times without obvious loss of its activity.

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“…Generally, the homogeneous palladium catalysts exhibit excellent activity and selectivity for the Suzuki‐Miyaura reaction owing to their uniformity on a molecular level and solubility in the reaction medium. Even so, the efficient separation and subsequent recycling of such expensive catalysts has remained a great challenge . Thus, recently, there has been an explosion in the development of heterogeneous catalytic systems in which palladium complexes are immobilized on various organic and inorganic supports to realize the ease of catalyst separation and recycling .…”

Section: Introductionmentioning

confidence: 99%

Encapsulation of a Palladium Schiff‐Base Complex into the Nanocages of Mesoporous SBA‐16 as an Efficient Heterogeneous Catalyst for the Suzuki‐Miyaura Coupling Reaction in Water

2019

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A palladium Schiff base complex was successfully encapsulated in the nanocages of SBA-16 by post-reducing the pore entrance size through a simple silylation method. The prepared material was demonstrated to be a high-performance and efficient heterogeneous catalyst in the Suzuki-Miyaura reaction of a wide range of aryl halides with arylboronic acids even with low palladium loading (0.01 mol%) under mild aqueous condition. The catalyst could be recovered by simple filtration from the reaction mixture and reused for eight cycles with no change in catalytic performance confirming its good stability. Comparison of the activity of free and encapsulated complex revealed that placement of the complex in the nanocages of SBA-16 did not compromise its catalytic activity. Moreover, based on the experimental results, we proposed a possible reaction mechanism, which was further confirmed by density functional theory (DFT) calculations.

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The effect of the hydrotalcite structure and nanoparticle size on the catalytic performance of supported palladium nanoparticle catalysts in Suzuki cross-coupling

Cited by 27 publications

References 67 publications

About Solid Phase vs. Liquid Phase in Suzuki-Miyaura Reaction

About Solid Phase vs. Liquid Phase in Suzuki-Miyaura Reaction

Synthesis, characterization and catalytic performance of palladium supported on pyridine‐based covalent organic polymer for Suzuki‐Miyaura reaction

Encapsulation of a Palladium Schiff‐Base Complex into the Nanocages of Mesoporous SBA‐16 as an Efficient Heterogeneous Catalyst for the Suzuki‐Miyaura Coupling Reaction in Water

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