Zeolite-encaged palladium catalysts for heterogeneous Suzuki-Miyaura cross-coupling reactions

Gao, Mingyang; Wang, Jiamin; Shang, Weixiang; Chai, Yuchao; Dai, Weili; Wu, Guangjun; Guan, Naijia; Li, Landong

doi:10.1016/j.cattod.2022.02.011

Cited by 23 publications

(13 citation statements)

References 48 publications

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“…By changing the halogen involved in the coupling reaction and considering Cl-benzene (entry 11) instead of Br-benzene (entry 8), we observed a decrease in yield from 93% to 55.5%. Once again, these values are in line with those reported for several heterogeneous supports [ 16 , 17 , 18 , 20 , 21 , 22 , 23 ].…”

Section: Resultssupporting

confidence: 91%

“…These values are reasonably good and comparable to many industrial catalytic processes, but are obtained by operating in the presence of an eco-friendly cellulose-derived palladium support. In fact, while we are aware that higher TONs can be obtained under homogeneous conditions, these values are comparable or even better than those of most of the examples reported in the literature for fixing Pd on heterogeneous supports [ 16 , 17 , 18 , 20 , 21 , 22 , 23 ]. Moreover, in this case, the choice of the support falls on a bio-based system derived from waste biomass.…”

Section: Resultssupporting

confidence: 69%

“…For these reasons, in recent years many solutions have been proposed for the immobilization of Pd(II)-precatalysts onto heterogeneous networks [ 16 , 17 , 18 , 19 ], also opening the route to continuous-flow synthetic processes [ 20 , 21 ]. However, in most cases the pre-functionalization of solid supports with proper ligands is necessary to guarantee high efficiency in fixing Pd(II), minimizing leaching phenomena [ 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

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Pd-Loaded Cellulose NanoSponge as a Heterogeneous Catalyst for Suzuki–Miyaura Coupling Reactions

Riva

Nicastro

Liu

et al. 2022

Gels

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The (eco)design and synthesis of durable heterogeneous catalysts starting from renewable sources derived from biomass waste represents an important step for reducing environmental impacts of organic transformations. Herein, we report the efficient loading of Pd(II) ions on an eco-safe cellulose-based organic support (CNS), obtained by thermal cross-linking between TEMPO-oxidized cellulose nanofibers and branched polyethyleneimine in the presence of citric acid. A 22.7% w/w Pd-loading on CNS was determined by the ICP-OES technique, while the metal distribution on the xerogel was evidenced by SEM–EDS analysis. XPS analysis confirmed the direct chelation of Pd(II) ions by means of the high number of amino groups present in the network, so that further functionalization of the support with specific ligands was not necessary. The new composite turned to be an efficient heterogeneous pre-catalyst for promoting Suzuki–Miyaura coupling reactions between aryl halides and phenyl boronic acid in water, obtaining yields higher than 90% in 30 min, by operating in a microwave reactor at 100 °C and with just 2% w/w of CNS-Pd catalyst with respect to aryl halides (4.5‰ for Pd). At the end of first reaction cycle, Pd(II) ions on the support resulted in being reduced to Pd(0) while maintaining the same catalytic efficiency. In fact, no leaching was observed at the end of reactions, and five cycles of recycling and reusing of CNS-Pd catalyst provided excellent results in terms of yields and selectivity in the desired products.

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Section: Resultssupporting

confidence: 91%

Section: Resultssupporting

confidence: 69%

Section: Introductionmentioning

confidence: 99%

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Pd-Loaded Cellulose NanoSponge as a Heterogeneous Catalyst for Suzuki–Miyaura Coupling Reactions

Riva

Nicastro

Liu

et al. 2022

Gels

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“…Li and coworkers prepared a catalyst by encaging palladium particles into K-ZSM-5 zeolite. [31] It was made by wet impregnation of Pd(NO 3 ) 2 into ZSM-5, followed by ion-exchange with KNO 3 and hydrogenation (10 % H 2 /Ar, 300 °C, 2 h), resulting in the formation of Pd particles of 1-2 nm (catalyst 0.7 wt% K-ZSM-5). Structural characterization was performed with XRD, TEM, and SEM.…”

Section: áGnes Mastalir (Born On 1 April 1962) Is Anmentioning

confidence: 99%

Palladium Nanoparticles Supported on Porous Silica Materials as Heterogeneous Catalysts of C−C Coupling and Cross‐Coupling Reactions

Mastalir

Molnár

2023

ChemCatChem

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Noble metal nanoparticles supported on porous silica materials represent an important class of heterogeneous catalysts. Various synthesis strategies have been developed, including the application of ligand‐assisted metal precursors, multistep synthesis procedures, post‐synthetic modifications, and magnetic mesoporous silica particles. Emphasis has been laid on the introduction of green procedures, based on the utilization of environmentally friendly solvents, efficient stabilizing agents, non‐toxic reagents, and mild reaction conditions. Palladium nanoparticles have long been recognized as the most efficient catalysts in a wide range of organic transformations, including the Heck, Suzuki, Stille, and Sonogashira reactions. Although these transformations have been extensively investigated in homogeneous catalytic systems, the application of heterogeneous catalysts, including silica‐supported Pd0 nanoparticles, has gained in increasing importance. The aim of this review is to provide an outlook on the current research progress achieved on the development of novel synthetic procedures, affording highly dispersed Pd0 nanoparticles immobilized on porous silica materials, which proved to be efficient and recyclable catalysts in C–C coupling and cross‐coupling reactions.

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“…Heterogeneous palladium catalysts anchored on different supports, inorganic and/or carbonaceous, have been used in cross-coupling reactions with remarkable result. [24][25][26][27][28][29] Photocatalytic [30][31][32][33] and in-flow cross-couplings setups [34,35] have also been developed as alternative solutions to classical homogeneous protocols. Despite extensive studies on various palladium sources as well as the development of new activephase supports, heterogeneous cross-coupling reactions catalyzed by solid-phase palladium species still suffer various issues linked to the loss of activity (i. e., metal leaching) that have seriously limited the exploitation of these catalysts on a proofof-concept ground.…”

Section: Introductionmentioning

confidence: 99%

Reduced Tiara‐like Palladium Complex for Suzuki Cross‐Coupling Reactions

Daka

Montini

Pengo

et al. 2023

Chemistry A European J

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The design of highly active and structurally well‐defined catalysts has become a crucial issue for heterogeneous catalysed reactions while reducing the amount of catalyst employed. Beside conventional synthetic routes, the employment of polynuclear transition metal complexes as catalysts or catalyst precursors has progressively intercepted a growing interest. These well‐defined species promise to deliver catalytic systems where a strict control on the nuclearity allows to improve the catalytic performance while reducing the active phase loading. This study describes the development of a very active and reusable palladium‐based catalyst on alumina (Pd8/Al2O3) for Suzuki cross coupling reactions. An octanuclear tiara‐like palladium complex was selected as active phase precursor to give isolated Pd‐clusters of ca. 1 nm in size on Al2O3. The catalyst was thoroughly characterised by several complementary techniques to assess its structural and chemical nature. The high specific activity of the catalyst has allowed to carry out the cross‐coupling reaction in 30 minutes using only 0.12 mol% of Pd loading under very mild and green reaction conditions. Screening of various substrates and selectivity tests, combined with recycling and benchmarking experiments, have been used to highlight the great potentialities of this new Pd8/Al2O3 catalyst.

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Zeolite-encaged palladium catalysts for heterogeneous Suzuki-Miyaura cross-coupling reactions

Cited by 23 publications

References 48 publications

Pd-Loaded Cellulose NanoSponge as a Heterogeneous Catalyst for Suzuki–Miyaura Coupling Reactions

Pd-Loaded Cellulose NanoSponge as a Heterogeneous Catalyst for Suzuki–Miyaura Coupling Reactions

Palladium Nanoparticles Supported on Porous Silica Materials as Heterogeneous Catalysts of C−C Coupling and Cross‐Coupling Reactions

Reduced Tiara‐like Palladium Complex for Suzuki Cross‐Coupling Reactions

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