Novel graphene-supported palladium complex catalyst with flexible-bridge-chains and its recycling carbon-carbon cross-coupling activity

Yang, Wenqing; Zhang, Yuqiang; Feng, Huiyi; Li, Shihao; Feng, Yi‐Si

doi:10.1016/j.apcata.2022.118852

Cited by 9 publications

(3 citation statements)

References 46 publications

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“…Subsequently, we optimized the catalyst and base, followed by a detailed investigation of the solvent system for the reaction. Other than protic polar solvents like ethanol and water, aprotic polar solvents such as toluene and acetonitrile (ACN), and even nonpolar solvents like 1,4-dioxane yielded low products even at 80 1C (Table SII, ESI † entries [15][16][17][18][19][20]. The use of aprotic polar solvents and non-polar solvents reduced the degree of decomposition of boronic acids and also slowed the rate of reaction.…”

Section: Resultsmentioning

confidence: 99%

“…[11][12][13][14] These properties make it versatile for rapidly growing catalytic applications. [15][16][17] Previous research has demonstrated the successful application of bimetallic nanoparticles as catalysts for the Suzuki-Miyaura (SM) cross-coupling reaction, facilitating the synthesis of biaryls from simple aryl halides and boronic acids. Although these methods are successful for simple biaryls, a 2012 study by Li et al employing Pd-Fe 3 O 4 @C with 52.5 wt% Pd for Suzuki coupling under reflux conditions lacked broader substrate applicability.…”

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confidence: 99%

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New conjugated carbazole derivatives: synthesis and photophysical properties catalysed by Pd–Cu@rGO

Bhagyalakshmi,

Indira,

Banu

et al. 2024

New J. Chem.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

New conjugated carbazole derivatives: synthesis and photophysical properties catalysed by Pd–Cu@rGO

Bhagyalakshmi,

Indira,

Banu

et al. 2024

New J. Chem.

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“…Recently, we have made an innovative exploration in the preparation of supported Pd catalysts, trying to graft Pd complexes with long and flexible carbon chains onto the surface of graphene through chemical bonding. [30] This graphenesupported Pd catalyst shows the respective advantages of both homogeneous and heterogeneous catalysts, so it could be called a quasi-homogeneous Pd catalyst. It can uniformly diffuse and float in the solvent under slight agitation, achieving macro homogeneity in the reaction system.…”

Section: Introductionmentioning

confidence: 99%

Effect of Flexible Chain Length of Graphene‐Supported Palladium Complex Catalyst on Suzuki‐Miyaura Coupling Activity

et al. 2023

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Three series of quasi‐homogeneous palladium catalysts (rGO‐L3‐nC‐Pd, n=4, 6, 8) for Suzuki‐Miyaura (S−M) coupling reactions were prepared by grafting organic palladium complexes with flexible chains of different lengths onto the surface of reduced graphene oxide (rGO) by covalent bonds. The Raman, FTIR, TGA, ICP‐MS, SEM and BET N2 adsorption techniques were employed to characterize the catalysts. The three rGO‐L3‐nC‐Pd catalysts were used in various S−M coupling reactions. At room temperature (RT), in H2O/EtOH mixed solvents, they showed excellent catalytic activity and recyclability for various aromatic substrates with different substituents or substituent positions. The results indicated that the catalytic activities of rGO‐L3‐nC‐Pd were closely related to the length of the flexible chain of the organic palladium complex bonded to the surface of rGO, that is, the longer the length of the flexible chain, the greater the activity of the catalyst. The order of catalytic activity is rGO‐L3‐8C‐Pd>rGO‐L3‐6C‐Pd>rGO‐L3‐4C‐Pd. This activity sequence did not change with different solvents, bases and substrates, even if the catalyst was recycled ten times. Our results may provide a new idea for the design of quasi‐homogeneous catalysts.

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New chelating N‐heterocyclic carbene palladium complexes immobilized on magnetic nanoparticles: Synthesis, characterization, and catalytic properties

Yang,

Liu,

Diao

et al. 2024

Applied Organom Chemis

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Two chelating N‐heterocyclic carbene (NHC) palladium complexes 3a‐b containing N‐(3‐bromopropyl)‐N′‐thioether difunctionalized imidazol‐2‐ylidene were synthesized by direct metalation of the precursor imidazolium salts and characterized by NMR and HR‐MS. The molecular structure of 3a has been further characterized unambiguously by X‐ray single crystal analysis. The subsequent substitution reaction with amine‐functionalized magnetic nanoparticles (MNPs‐NH2) afforded two highly active, stable, and recyclable magnetic nanoparticle supported NHC palladium complexes, MNPs‐NHC‐Pd I‐II, which were characterized by Fourier transform infrared spectroscopy (FT‐IR), X‐ray diffraction (XRD), inductively coupled plasma optical emission spectrometry (ICP‐OES), scanning electron microscopy (SEM), and X‐ray photoelectron spectroscopy (XPS). The MNPs‐NHC‐Pd complexes exhibited high catalytic activity in the Suzuki–Miyaura cross‐coupling reaction of aryl bromides with arylboronic acids, as well as in the reduction of toxic 4‐nitrophenol (4‐NP) under mild conditions. The recycling experiment of MNPs‐NHC‐Pd I in the Suzuki–Miyaura cross‐coupling reaction between 4‐bromoanisole and phenylboronic acid showed that the yield of 4‐methoxybiphenyl remained high at 88% within 0.5 h at 60 °C, indicating that the catalytic activity was well maintained for at least 10 cycles.

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Novel graphene-supported palladium complex catalyst with flexible-bridge-chains and its recycling carbon-carbon cross-coupling activity

Cited by 9 publications

References 46 publications

New conjugated carbazole derivatives: synthesis and photophysical properties catalysed by Pd–Cu@rGO

New conjugated carbazole derivatives: synthesis and photophysical properties catalysed by Pd–Cu@rGO

Effect of Flexible Chain Length of Graphene‐Supported Palladium Complex Catalyst on Suzuki‐Miyaura Coupling Activity

New chelating N‐heterocyclic carbene palladium complexes immobilized on magnetic nanoparticles: Synthesis, characterization, and catalytic properties

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