Covalent organic framework‐supported Pd nanoparticles: An efficient and reusable heterogeneous catalyst for Suzuki–Miyaura coupling reactions

Jin, Hao; Zhang, Chi; Liu, Pingwei; Ge, Xin; Zhou, Shaodong

doi:10.1002/aoc.6642

Cited by 13 publications

(14 citation statements)

References 63 publications

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“…Therefore, the newly prepared Pd@COF-TB nanocatalyst here was only characterized by Fourier transform infrared spectroscopy (FT-IR) to confirm its correct structure. As shown in Figure 2 , the FT-IR absorption spectrum of the newly prepared Pd@COF-TB nanocatalyst was identical to the nanocatalyst prepared in our previous work [ 34 ], which means they have the same structure.…”

Section: Resultssupporting

confidence: 63%

“…The preparation of the Pd@COF-TB nanocatalyst was carried out according to the method established in our previous work [ 34 ] and its characterization also has been reported in detail. Therefore, the newly prepared Pd@COF-TB nanocatalyst here was only characterized by Fourier transform infrared spectroscopy (FT-IR) to confirm its correct structure.…”

Section: Resultsmentioning

confidence: 99%

“…A Schlenk tube was used for the addition of COF-TB (200 mg), Pd(OAc) 2 (20 mg) and Diox (60 mL), followed by agitation at 70 °C for 15 h. After that, a yellow–green solid was obtained by high-speed centrifugation. Subsequently, the solid was washed and filtered with acetonitrile, and dried overnight in a fume hood to obtain a yellow–green powder of the Pd@COF-TB nanocatalyst (208.6 mg) [ 34 ].…”

Section: Methodsmentioning

confidence: 99%

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Efficient Construction of Symmetrical Diaryl Sulfides via a Supported Pd Nanocatalyst-Catalyzed C-S Coupling Reaction

Jin

Liu

Teng

et al. 2022

IJMS

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Aryl sulfides play an important role in pharmaceuticals, biologically active molecules and polymeric materials. Herein, a general and efficient protocol for Pd@COF-TB (a kind of Pd nanocatalyst supported by a covalent organic framework)/DIPEA-catalyzed one-pot synthesis of symmetrical diaryl sulfides through a C-S coupling reaction from aryl iodides and Na2S2O3 is developed. More importantly, the addition of N,N-diisopropylethylamine (DIPEA) can not only enhance the catalytic activity of a Pd@COF-TB nanocatalyst, but also effectively inhibit the formation of biphenyl byproducts, which are a product of Ullmann reaction. Besides, it has been confirmed that the aryl Bunte salts generated in situ from Na2S2O3 and aryl iodides are the sulfur sources involved in this C-S coupling reaction. With the strategy proposed in this work, a variety of symmetrical diaryl sulfides could be obtained in moderate to excellent yields with a high tolerance of various functional groups. Moreover, a possible mechanism of this Pd nanoparticle-catalyzed C-S coupling reaction is proposed based on the results of controlling experiments.

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Section: Resultssupporting

confidence: 63%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Efficient Construction of Symmetrical Diaryl Sulfides via a Supported Pd Nanocatalyst-Catalyzed C-S Coupling Reaction

Jin

Liu

Teng

et al. 2022

IJMS

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“…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%

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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“…They have demonstrated promising uses in gas storage and separation, heterogeneous catalysis, optoelectronic materials, and energy storage [16][17][18][19][20][21]. Among various applications, 2D COFs are considered as ideal platforms for MNP supports [22][23][24][25]: First of all, COFs have pre-designable well-defined pore structures which can be employed to constrain MNP growth and thus control the size of MNPs; Secondly, the pore channels in COFs are well-isolated, hence minimizing the aggregation of entrapped MNPs [26,27]. Finally, many COFs are stable, which makes them resistant toward decomposition under various reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

2D Microporous Covalent Organic Frameworks as Cobalt Nanoparticle Supports for Electrocatalytic Hydrogen Evolution Reaction

et al. 2022

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Covalent organic frameworks (COFs) are a new class of porous crystalline polymers, which are considered to be excellent supports for metal nanoparticles (MNPs) due to their highly ordered structure, chemical tunability, and porosity. In this work, two novel ultra-microporous COFs, JUC−624 and JUC−625, with narrow pore size distribution have been synthesized and used for the confined growth of ultrafine Co nanoparticles (CoNPs) with high loading. In an alkaline environment, the produced materials were investigated as electrocatalysts for the hydrogen evolution reaction (HER). Electrochemical test results show that CoNPs@COFs have a Tafel slope of 84 mV·dec−1, an onset overpotential of 105 mV, and ideal stability. Remarkably, CoNPs@JUC−625 required only 146 mV of overpotential to afford a current density of 10 mA cm−2. This research will open up new avenues for making COF-supported ultrafine MNPs with good dispersity and stability for extensive applications.

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Covalent organic framework‐supported Pd nanoparticles: An efficient and reusable heterogeneous catalyst for Suzuki–Miyaura coupling reactions

Abstract: eight times without obvious decrease in activity and selectivity. More importantly, the leaching of Pd during the reaction process could be negligible, which is crucially important when preparing bioactive species.

Cited by 13 publications

References 63 publications

Efficient Construction of Symmetrical Diaryl Sulfides via a Supported Pd Nanocatalyst-Catalyzed C-S Coupling Reaction

Efficient Construction of Symmetrical Diaryl Sulfides via a Supported Pd Nanocatalyst-Catalyzed C-S Coupling Reaction

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

2D Microporous Covalent Organic Frameworks as Cobalt Nanoparticle Supports for Electrocatalytic Hydrogen Evolution Reaction

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