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Suzuki-Miyaura反应
APPLIED SURFACE SCIENCE · 2025 · IF 6.9

Palladium immobilized on lignin-based hypercrosslinked polymers as robust and efficient heterogeneous catalyst for Suzuki-Miyaura reactions in water

You Shu,De-Xuan Xiang,Man-Ying Li,Xiao-Ru Xie,Qing-Yao Chen,Yi-Ting Lin,Zhi-Yong Yang,Yue-jun Ouyang,Gui Chen

Lignin is an important organic polymer and a potential renewable resource. In this work, two novel palladium immobilized on lignin-based hypercrosslinked polymers were successfully fabricated via the Friedel-Crafts alkylation reaction and metallization. The protocol is associated with mild conditions, low cost, high yield, easy separation. The structure of the catalysts were studied by FT-IR, N 2 sorption, XPS, ICP, TGA, TEM, and SEM. Analysis indicates that the polymers exhibit significant characteristics such as large pore volume, highly distributed palladium, excellent chemical and thermal stability, and high specific surface areas. Subsequently, the heterogeneous catalysts were deployed within the context of the Suzuki-Miyaura reaction as a means to evaluate their catalytic activity. In the realm of aqueous environments, HCP-L&Pd-I showcases remarkable efficiency in catalyzing the Suzuki-Miyaura reaction, which benefited from the synergistic effect between the hierarchical pore structure in the material and numerous hydroxyl groups in lignin coordinating with palladium. Under optimum conditions, 0.1 mol% Pd content was enough to react with 97 % yield of biphenyl. Moreover, the catalyst was simply regenerated and reused six times without significant activity loss. This protocol perhaps provides a new perspective on the effective preparation of biphenyl aromatic compounds utilizing lignin-based heterogeneous catalysts in the Suzuki-Miyaura reaction.

研究领域: 化学 · 材料科学
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MATERIALS CHEMISTRY AND PHYSICS · 2018 · IF 2.21

Cost-effective nitrogen-doped carbon black supported PdCu alloy nanocatalyst for green Suzuki-Miyaura reactions under mild conditions

Jiawei Xia,Yongsheng Fu,Guangyu He,Xiaoqiang Sun,Xin Wang

A nitrogen-doped carbon black (NCB) supported PdCu alloy nanocatalyst is fabricated via a facile one-pot soft chemistry route. The PdCu nanoparticles are uniformly dispersed on the NCB surface with an average size of 3.51 nm. The PdCu/NCB catalyst exhibits superior catalytic activity and significantly improved durability towards the Suzuki-Miyaura coupling reaction in ethanol/water system under mild conditions without a protective atmosphere . Particularly, the Pd5Cu5/NCB catalyst can efficiently catalyzed the SMC reaction with the yield up to 94% in 1.5 h, 7-fold higher than that by the pristine Pd/NCB catalyst (13%). Compared with the carbon black supported PdCu catalyst, nitrogen-doping can lead to better dispersion of the PdCu alloy nanoparticles on the NCB surface with a smaller particle size. The excellent catalytic performance can be attributed to the unique nanostructure of the catalyst and concerted effect of the individual components. Notably, alloying Pd with Cu can effectively reduce the cost of the catalyst.

研究领域: 材料科学 · 催化化学
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JOURNAL OF MOLECULAR STRUCTURE · 2023 · IF 3.8

Palladium nanoparticles immobilized on N-decorated porous carbon as synergistic catalyst for carbon-carbon coupling reactions

Bin Zhao,Ningzhao Shang,Shutao Gao,Chun Wang

N -decorated porous carbon (NDC) was obtained by one step direct pyrolysis of NH 2 -MIL-125. The content of nitrogen in the NDC-1000 (2 h) was 4.2%. Palladium nanoparticle was deposited on the NDC by an impregnation strategy. The NDC-1000-Pd catalyst was characterized by powder X-ray diffraction, TEM, XPS and N 2 adsorption. Due to the synergetic interaction of metal species and NDC, the catalyst exhibited excellent catalytic performance for Heck coupling and Suzuki-Miyaura reactions. The catalyst can be reused for five cycles without obvious change in its activity.

研究领域: 化学催化 · 材料科学
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Catalysis Science & Technology · 2012 ·Vol. 2 ·期 11 ·2332-2340 · IF 0

A facile preparation of palladium nanoparticles supported on magnetite/s-graphene and their catalytic application in Suzuki–Miyaura reaction

Jiefeng Hu,Yuping Wang,Min Han,Yaoming Zhou,Xiaoqing Jiang,Peipei Sun

Fe3O4 and Pd nanoparticles were assembled on sulfonated graphene (s-G) by an easy chemical approach and characterized by transmission electron microscopy, X-ray diffraction and energy dispersive X-ray spectroscopy. The resulting material could be dispersed homogeneously in water or water/ethanol and further used as an excellent semi-heterogeneous catalyst for the Suzuki–Miyaura cross-coupling reaction in an environmentally friendly solvent under ligand-free ambient conditions. The high heterogeneous catalytic activity appears to be due to the small size of Pd nanoparticles and homogeneous distribution of the nanoparticles on the Fe3O4/s-G matrix. In addition, the catalytic activity did not deteriorate even after repeated applications, which may be due to the easy and efficient magnetic separation of the catalyst and the high dispersion and stability of the catalyst in an aqueous solution.

研究领域: 材料科学 · 催化化学
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MACROMOLECULAR RESEARCH · 2019 ·Vol. 27 ·期 10 ·931-937 · IF 1.758

Triphenylphosphine-Containing Thermo-Responsive Copolymers: Synthesis, Characterization and Catalysis Application

Chen Tao,Zhang Shuo,Hua Laiyu,Xu Zhenkai,Zhou Lei,Wang Jiping

Triphenylphosphine-containing thermo-responsive copolymers of 4-(diphenylphosphino) styrene (DPPS), di(ethylene glycol) methyl ether methacrylate (DEGMA) and oligo(ethylene glycol) methyl ether methacrylate (average molecule weight is 300, OEGMA 300 ) were synthesized by free-radical copolymerization using azodiisobutyronitrile (AIBN) as an initiator in solution polymerization. A series of copolymers P(DEGMA- co -DPPS- co -OEGMA 300 ) with different lower critical solution temperature (LCST) were synthesized. The synthesized copolymers were well characterized by 1 H NMR, 31 P NMR and gel permeation chromatography (GPC). Based on the copolymers, a thermo-responsive and water soluble assembled catalyst of palladium acetate was developed. In the presence of the thermo-responsive copolymer-supported palladium catalyst, the Suzuki-Miyaura reaction proceeded efficiently in water. The catalyst was reused at least five cycles without obvious decrease in catalytic activity and can be easily recovered by heating/centrifugation of the polymer aqueous solution.

研究领域: 高分子化学 · 催化化学 · 有机合成
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RSC Advances · 2013 ·Vol. 3 ·期 44 ·21863-21868 · IF 2.562

Graphene oxide supported N-heterocyclic carbene-palladium as a novel catalyst for the Suzuki–Miyaura reaction

Ningzhao Shang,Shutao Gao,Cheng Feng,Haiyan Zhang,Chun Wang,Zhi Wang

In this paper, an N-heterocyclic carbene–palladium complex (NHC-Pd2+) was immobilized onto the surface of graphene oxide via a chemical bonding method for the first time. The resultant graphene oxide supported NHC–Pd2+ composite (GO supported NHC-Pd2+) was characterized by transmission electron microscopy, X-ray diffraction spectroscopy, X-ray photoelectron spectroscopy and infrared spectroscopy. It was demonstrated that the GO supported NHC-Pd2+ can act as an efficient catalyst for Suzuki–Miyaura coupling reactions. The yields of the products were in the range of 83% to 96%. The catalyst can be readily recovered and reused for at least 6 consecutive cycles without any significant loss in catalytic activity.

研究领域: 材料科学 · 有机化学
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CATALYSIS COMMUNICATIONS · 2016 · IF 3.389

Highly efficient palladium catalysts supported on nitrogen contained polymers for Suzuki-Miyaura reaction

Longfei Geng,Yan Li,Zhengliang Qi,Haipeng Fan,Zhicheng Zhou,Rizhi Chen,Yong Wang,Jun Huang

Through Pd catalyzed C N coupling reaction, Pd nanoparticles and diadamantylphosphine ligand were immobilized in situ into the formed N contained polymers as heterogeneous Pd catalysts for Suzuki-Miyaura reaction. The Pd@NPad 2 -1.0 catalyst was found to be highly efficient and only 4   ppm of Pd (Pd@NPad 2 -1.0) was required for the coupling of aryl bromides with phenylboronic acid, and the corresponding products were obtained in good to excellent yields with high TON and TOF as 250,000 and 41,666   h −   1 respectively. Moreover, the coupling of various aryl chlorides with phenylboronic acids gave the corresponding products in high yields also. And the Pd@NPad 2 -1.0 catalyst is reusable at least 5 times with only slight deactivation.

研究领域: 化学 · 催化材料科学
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Molecular Catalysis · 2017 · IF 0

A simple method for preparing imidazolium-based polymer as solid catalyst for Suzuki-Miyaura reaction

Weiqiang Zhang,Liangyi Peng,Chunyan Deng,Yingxue Zhang,Hao Qian

Polymers containing the structure of N-heterocyclic carbenes (NHCs) have attracted much interest due to their superior complexing ability to metal ions and good recyclability, which make them promising candidates as solid supporters. Herein, we developed an easy method to synthesize polyimidazolium chloride salt (PImCl) via one-step method in mild conditions. After PImCl was chelated with palladium chloride in 3-chloropyridine, this NHC-Pd polymer was employed as the solid catalyst for Suzuki reactions of aryl bromides and phenylboronic acid. The catalytic activity of the NHC-Pd polymer was high for many different substrates. Moreover, the Suzuki reaction of 4-bromoanisole with phenylboronic acid could be catalyzed by this NHC-Pd polymer in mild conditions. Furthermore, this solid catalyst could be easily isolated by centrifugal separation. After several recycling runs, the catalytic activity decreased little. Compared with the conventional methods, this method was much simpler and more efficient, which showed enormous potential in preparing new heterogeneous supporter of porous polyimidazolium chloride salt.

研究领域: 有机化学 · 催化化学
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CATALYSIS LETTERS · 2024 ·Vol. 155 ·期 1 ·1-10 · IF 2.3

Palladium-Based Catalyst on L-Histidine-Modified Boron Nitride Nanosheets: A Novel, Stable, and Highly Efficient Heterogeneous Catalyst for Suzuki–Miyaura Reaction

Wang Xu,Li Guohua,Feng Guo,Wang Yajie,Sun Hongxin

In this study, we developed a multiphase catalyst, BNNSs/His-Pd, by anchoring palladium nanoparticles onto L-histidine-modified boron nitride nanosheets. BNNSs/His-Pd was shown to be a good 2D heterogeneous catalyst. The enhanced affinity of the modified BNNSs for metal complexes, coupled with their inherent stability, contributes to the catalytic activity of the BNNSs/His-Pd-catalyzed Suzuki coupling reaction. The catalyst showed a broad substrate scope, good catalytic activity, and the convenience of not requiring inert gas protection in the Suzuki–Miyaura cross-coupling reaction. Even after 10 recycling cycles, the product yield remained at 95%, highlighting its significant potential for practical applications. Graphical Stable and efficient BNNSs/His-Pd heterogeneous catalysts were successfully constructed by modifying boron nitride nanosheets with L-histidine. The effect of L-histidine enhanced the dispersion and stability of Pd NPs on BNNSs carriers, combined with the inherent stability of BNNSs which resulted in the improvement of catalytic activity and recycling performance of the catalysts in the Suzuki coupling reaction.

研究领域: 材料科学 · 催化化学
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ACS Catalysis · 2024 · IF 11.3

Unveiling Plasmon-Induced Suzuki–Miyaura Reactions on Silver Nanoparticles via Raman Spectroscopy

Yunjia Wei,Dexiang Chen,Xingce Fan,Xiao Tang,Lei Yao,Xing Zhao,Qiang Li,Jiawei Wang,Teng Qiu,Qi Hao

The Suzuki–Miyaura coupling reaction is an efficient organic method for synthesizing biphenyl products. However, its conventional reliance on toxic soluble organometallic palladium catalysts or expensive palladium nanoparticles, along with the need for elevated temperatures and prolonged reaction times, presents a significant challenge. Herein, we demonstrate a palladium-free approach using plasmonic silver nanoparticles that enables the Suzuki–Miyaura coupling reaction to proceed at room temperature under visible light. Utilizing the surface-enhanced Raman scattering characteristics of silver, we conducted dynamic self-monitoring of the reaction. Our findings reveal that this plasmon-induced Suzuki–Miyaura coupling reaction fundamentally operates as a heterogeneous reaction involving coupling between radicals, distinct from conventional palladium-based reactions. Moreover, the cleavage of C–Cl and C–B bonds, fundamental prerequisite to the coupling, is driven by plasmonic hot electrons and plasmon-induced reactive oxygen species, respectively. These findings not only provide insights into the design and regulation of plasmonic catalysts but also enhance theoretical understanding of the Suzuki–Miyaura reaction in a broader context.

研究领域: 化学 · 材料科学 · 光催化
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JOURNAL OF MOLECULAR STRUCTURE · 2020 · IF 2.463

Bulky α-diimine palladium complexes supported graphene oxide as heterogeneous catalysts for Suzuki-Miyaura reaction

Ning Liu,NiNa Qiao,Feng-Shou Liu,ShaoHua Wang,Ying Liang

To explore high efficiency of the Suzuki-Miyaura reactions, an easily prepared heterogeous palladium precatalysts bearing sterically bulky α-diimine was covalently supported on graphene oxide (GO). The characterization of supported palladium complex was discussed in detail. A simple and efficient protocol for Pd-catalyzed cross coupling was described, which revealed that the bulky α-diimine ligand is crucial to promote the C Ar -C Ar transformation. This immobilized system provides a straightforward access to a wide range of aryl bromides with excellent functional groups tolerance.

研究领域: 化学 · 材料科学 · 有机合成
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RSC Advances · 2014 ·Vol. 4 ·期 58 ·30914-30922 · IF 3.708

Fast synthesis of Ag–Pd@reduced graphene oxide bimetallic nanoparticles and their applications as carbon–carbon coupling catalysts

Mingxi Chen,Zhe Zhang,Lingzhi Li,Yu Liu,Wei Wang,Jianping Gao

Ultrafine Ag–Pd bimetallic nanoparticles homogeneously distributed on reduced graphene oxide (rGO) were prepared by redox reactions between Pd2+, Ag+ and GO. This method is simple, and the use of rGO as a support facilitated the separation and reuse of the Ag–Pd@rGO catalyst. The Ag–Pd@rGO bimetallic nanoparticles were characterized by ultraviolet-visible spectroscopy, Raman spectroscopy, thermogravimetric analysis, X-ray diffraction analysis, and X-ray photoelectron spectroscopy. The microstructure of the Ag–Pd@rGO was investigated with scanning electron microscopy and transmission electron microscopy. The Ag–Pd@rGO catalyst exhibited high catalytic activities in the Suzuki-Miyaura carbon coupling reaction and the Sonogashira carbon coupling (SCC) reaction. These reactions used mild, efficient, ligand-free and heterogeneous conditions. Interestingly, the presence or absence of oxygen in the SCC catalytic system resulted in two different products, in which oxygen can be used as “switch” to control different products.

研究领域: 材料科学 · 催化化学
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