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Suzuki反应
APPLIED ORGANOMETALLIC CHEMISTRY · 2017 ·Vol. 31 ·期 12 ·e3854 · IF 2.319

Novel cyclodextrin-modified h-BN@Pd(II) nanomaterial: An efficient and recoverable catalyst for ligand-free C-C cross-coupling reactions in water

Xiaojun Ma,Guanghui Lv,Xu Cheng,Weijian Li,Rui Sang,Yong Zhang,Qiantao Wang,Li Hai,Yong Wu

An environmentally friendly palladium(II) catalyst supported on cyclodextrin-modified h-BN was successfully prepared. The catalyst was characterized by FT-IR, SEM, TG, XRD and XPS, and the loading level of Pd in h-BN@β-CD@Pd(II) was measured to be 0.088 mmol g −1 by ICP. It exhibits excellent catalytic activity for the Suzuki and Heck reactions in water, and can be easily separated and consecutively reused for at least nine times. In addition, a series of pharmacologically interesting products were successfully synthesized using this catalyst to demonstrate its potential applications in pharmaceutical industries. Above all, this work opens up an interesting and attractive avenue for the use of cyclodextrin-functionalized h-BN as an efficient support for hydrophilic heterogeneous catalysts.

研究领域: 材料科学 · 催化化学
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CARBOHYDRATE POLYMERS · 2021 · IF 9.381

Functionalized chitosan as a novel support for stabilizing palladium in Suzuki reactions

Yahao Dong,Jiajun Bi,Shujun Ming,Shoute Zhang,Dajian Zhu,Di Meng,Tao Li

Chitosan is a versatile polysaccharide in different domains due to facile modification and good biodegradability. In this paper, taking advantage of such functional properties, we have developed a stabilizer agent [OCMCS-SB] produced from chitosan, and palladium was successfully immobilized on this designed stabilizer [OCMCS-SB-Pd(II)]. The obtained complex was illuminated by 13 C CP-MAS NMR, FT-IR, TGA, XRD, XPS, SEM, TEM and ICP-OES analyses. Due to the interactions of primary hydroxyl groups on chitosan, Schiff base and carboxy groups, the Pd complex showed excellent reactivity (up to 99 %) and stability towards Suzuki reactions in eco-friendly medium. Subsequently, the reusability experiments for OCMCS-SB-Pd(II) formed from chitosan were examined in five consecutive cycles, which showed no appreciable decrease in activity. Furthermore, a reasonably trifunctional complex structure was proposed. The present bio-based system offers a promising approach in utilizing such biopolymers in organic transformations.

CAS / MDL: 121-33-5
研究领域: 生物化学 · 有机化学 · 材料科学
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JOURNAL OF NANOSCIENCE AND NANOTECHNOLOGY · 2011 ·Vol. 11 ·期 9 ·7794-7801 · IF 1.352

Microwave-Assisted Facile Synthesis of Palladium Nanoparticles in HEPES Solution and Their Size-Dependent Catalytic Activities to Suzuki Reaction

Zhang Wei,Wang Qiao,Qin Fan,Zhou Huamin,Lu Zhong,Chen Rong

Palladium nanoparticles (NPs) were successfully synthesized via a rapid and facile microwave route in HEPES (2-[4-(2-hydroxyethyl)-1-piperazinyl]ethanesulfonic acid) buffer solution. The shape- and size-controlled Pd nanoparticles could be obtained by one-step method without dependence of seed-mediated growth. The capping agent plays a key role in the formation of Pd NPs with different shape and size, which could be tuned by varying capping agents such as polyvinylpyrrolidone (PVP), cetyltrimethylammonium bromide (CTAB), sodium citrate (Na3(cit)) and potassium bromide (KBr). The size-dependent catalytic activities of the obtained Pd NPs for Suzuki coupling reaction were also investigated. It demonstrated that the catalytic activity of Pd NPs was enhanced regularly with the decrease of particle size. Pd NPs less than 10 nm exhibited better catalytic activities for Suzuki reaction than the commercial Pd/C catalyst. Pd/MWCNTs and Pd/SBA-15 nanocomposites were also prepared by a facile method and afforded good catalytic activity and reusability. This "green" synthetic protocol could be used as a general method for the rapid synthesis of transition metal nanoparticles.

研究领域: 化学 · 材料科学 · 催化反应
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JOURNAL OF PHYSICS AND CHEMISTRY OF SOLIDS · 2022 · IF 4.383

Correlation of adsorbed and embedded palladium species in chitosan composite nanofibers with their catalytic activities for Suzuki reactions

Baogang Su,Qi Zhang,Linjun Shao,Shujing Zhou,Jinjing Li,Yijun Du,Chenze Qi

Heterogeneous palladium catalysts play an important role in the synthetic organic chemistry. Palladium species have been adsorbed on the surface of solid matrices or embedded inside solid matrices to prepare recyclable heterogeneous catalysts. Due to the different surrounding environment, these two type palladium species had different electronic properties and catalytic performances. In this study, we fabricated three series of chitosan composite nanofibers with adsorbed and embedded palladium species. Their fiber morphologies and chemical structures were characterized by SEM and FT-IR, respectively. Positron annihilation lifetime spectra (PALS) showed that the intensities (I 3 ) of o -Ps annihilations were all linearly decreased with the increase of palladium contents in the chitosan composite nanofibers. Moreover, compared with the palladium adsorbed chitosan composite nanofibers, the palladium embedded chitosan composite nanofibers had stronger o -Ps annihilation ability, which could be ascribed to the stronger electron donating property of embedded palladium species and higher crosslinking of chitosan molecules by embedded palladium species. At last, the I 3 values were successfully correlated with the rate constants of chitosan supported palladium composite nanofibers catalyzed Suzuki reactions of iodobenzene with phenylboric acid. Therefore, we have developed a facile method to distinguish the adsorbed and embedded palladium species by PALS, which can be further related with their catalytic performance.

CAS / MDL: 100-60-7 9002-88-4
研究领域: 有机化学 · 催化材料科学
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Catalysis Science & Technology · 2012 ·Vol. 3 ·期 4 ·952-961 · IF 0

Hematite nanoparticle-templated hollow carbon nanonets supported palladium nanoparticles: preparation and application as efficient recyclable catalysts

Maiyong Zhu,Ying Wang,Chengjiao Wang,Wei Li,Guowang Diao

Hollow carbon nanonets (HCN), which are attractive materials for catalyst support, were fabricated using the pre-synthesized hematite nanoparticles as the hard template. And then the HCN supported Pd nanoparticles (Pd/HCN) were prepared by precipitation-reduction method. The catalytic performance of Pd/HCN was investigated using Suzuki and Heck coupling reactions as model reactions. The results demonstrated that the as-prepared Pd/HCN nanocomposites exhibit high catalytic activity for the two types of coupling reactions under ligand free conditions. Especially, the Suzuki reactions between various aryl halides and phenylboronic acid gave excellent yields in water. Moreover, the as-prepared Pd/HCN catalysts can be easily recovered from the reaction medium by centrifugation for recycling, and the catalytic efficiency shows no obvious loss even after 6 repeated cycles.

研究领域: 材料科学 · 化学工程 · 纳米技术
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JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY · 2018 ·Vol. 56 ·期 20 ·2344-2353 · IF 2.588

Polymer-supported palladium (II) containing N2O2: An efficient and robust heterogeneous catalyst for C–C coupling reactions

Jiajun Bi,Jian Chen,Yahao Dong,Wen Guo,Dajian Zhu,Tao Li

A new polymer was prepared from 1,3,5-triformylphloroglucinol (noted as TDTB) and o -phenylenediamine through Schiff base condensation reaction, and palladium (II) was immobilized on the polymer (noted as TbPo-Pd(II)). This process was easy to work-up and cost-effective. The structure and composition of TbPo-Pd(II) were fully characterized by FTIR, TGA, XPS, AAS, SEM, and TEM analyses. Meanwhile, this catalyst showed desired thermal stability and excellent performance in water/methanol system for Suzuki and Sonogashira coupling reactions. In addition, this heterogeneous catalyst can be readily recovered by simple filtration with no appreciable Pd leaching in the reaction. This work provides a powerful protocol for rapid access to asymmetrical biphenyls and aryl alkynes. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 , 56 , 2344–2353

研究领域: 有机化学 · 材料科学
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ACS Omega · 2024 · IF 3.7

Excellent Pd-Loaded Magnetic Nanocatalyst on Multicarboxyl and Boronic Acid Biligands

Haijiao Jia,Mengqi Cheng,Ran Zhao,Pingyi Zheng,Fangfang Ren,Yaqin Nan,Mengting Huang,Youxin Li

An effective palladium nanocatalyst (Fe3O4@SiO2–FPBA–DTPA–Pd) was proposed and prepared, which was immobilized on magnetic silica with ethylenediamine pentaacetic acid and formylphenylboronic acid as biligands. A series of characterizations showed that Fe3O4@SiO2–FPBA–DTPA–Pd was 5–15 nm and contained 1.44 mmol/g Pd2+/Pd0. It was stable below 232.7 °C, and its saturation magnetization value was 21.17 emu/g which was easily recycled by a magnet. Its catalytic ability was evaluated through 7 Suzuki reactions and 15 Heck reactions. Results showed that the yields of 14 reactions catalyzed by Fe3O4@SiO2–FPBA–DTPA–Pd were more than 90%, while were better than those of the other two immobilized Pd catalysts on a single diethyltriamine pentaacetic acid (DTPA) group or boronic acid group. Moreover, Fe3O4@SiO2–FPBA–DTPA–Pd showed good reusability in both Suzuki and Heck reactions. In two model Suzuki and Heck reactions, after seven cycles, its yields were still above 95% without significant loss, which exceeded those of many reported catalysts; therefore, it has great potential in future large-scale industrial production.

研究领域: 化学 · 材料科学
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APPLIED ORGANOMETALLIC CHEMISTRY · 2021 ·Vol. 35 ·期 12 ·e6445 · IF 4.105

Palladium nanoparticles encapsulated in polyimide nanofibers: An efficient and recyclable catalyst for coupling reaction

Yijun Du,Faliang Gou,Danning Gao,Zhifeng Liu,Linjun Shao,Chenze Qi

In this study, palladium-encapsulated poly(amic acid) (Pd@PAA) nanofibers were prepared by electrospinning, followed by thermal imidization to synthesize palladium-encapsulated polyimide (Pd@PI) nanofibers. Scanning electron microscopy (SEM) images confirmed the preparation of uniform and smooth Pd@PAA and Pd@PI nanofibers. Thermogravimetric analysis (TGA) results reveal that the Pd@PI nanofibers possessed excellent thermal stability. The dispersion of palladium nanoparticles in the polyimide nanofibers was characterized by transmission electron microscopy (TEM) and X-ray diffraction (XRD). The catalysis results show that this Pd@PI fibrous catalyst was very efficient to catalyze the cross-coupling reactions of aromatic iodides with n -butyl acrylate (Heck reaction) or phenylboronic acid derivatives (Suzuki reaction) to afford the desired products in good to excellent yields. Moreover, the Pd@PI catalyst could be easily separated and recovered from the reaction mixture by simple filtration due to the regular fibrous structure and reused for 10 times for both Heck and Suzuki reactions without obvious loss of its initial catalytic activity. Thus, the Pd@PI nanofiber catalyst holds great potential in chemical industry in terms of its excellent catalytic activity and stability.

研究领域: 材料科学 · 化学工程
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Nano Research · 2014 ·Vol. 7 ·期 9 ·1337-1343 · IF 6.963

Bimetallic Pd-Ni core-shell nanoparticles as effective catalysts for the Suzuki reaction

Xiang Ji,Li Peng,Chong Hanbao,Feng Li,Fu Fangyu,Wang Zhuang,Zhang Shilin,Zhu Manzhou

A simple and efficient solution-based method for the synthesis of Pd-Ni bimetallic nanoparticles (NPs) has been developed. A series of Pd-Ni bimetallic NPs were readily achieved by reduction of PdCl 2 and Ni(acac) 2 (acac = acetylacetonate) in the presence of oleylamine (OAm), oleic acid (OA) and benzyl alcohol. Furthermore, by using high-resolution transmission electron microscopy (HRTEM), energy-dispersive spectrometry (EDS) mapping and X-ray diffraction (XRD), we demonstrate that the as-prepared Pd-Ni bimetallic NPs have core-shell structures with a Pd-rich core and a Ni-rich shell. In addition, the as-obtained Pd-Ni bimetallic NPs with varying compositions show excellent catalytic activities in the Miyaura-Suzuki reaction. When the nickel molar percentage was 0.23 to 0.65, the conversion with the as-obtained Pd-Ni bimetallic catalysts was above 90%. It is believed that this strategy can be employed to produce a variety of other well-defined core-shell type multimetallic nanostructures.

研究领域: 材料科学 · 化学
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APPLIED SURFACE SCIENCE · 2020 · IF 6.182

Palladium supported on N-Heterocyclic carbene functionalized hydroxyethyl cellulose as a novel and efficient catalyst for the Suzuki reaction in aqueous media

Yahao Dong,Jiajun Bi,Shoute Zhang,Dajian Zhu,Di Meng,Shujun Ming,Kaiwei Qin,Qian Liu,Lei Guo,Tao Li

Bearing an intrinsic green nature, biopolymers are expected to serve as ideal alternatives in the sustainable conversion process. In this paper, a N -Heterocyclic carbene functionalized hydroxyethyl cellulose supported palladium catalyst (HEC-NHC-Pd) has been successfully prepared through a surface functionalization approach. The as-prepared catalyst was characterized through TEM, CP/MAS 13 C NMR, and XPS analyses, etc. The new and eco-friendly catalyst was effectively employed in Suzuki reactions in ethanol aqueous solution. Dependent on dual coordination sites ( OH and N -Methylimidazole) binding to the active component (Pd), the palladium complex exhibited high stability and low metal leaching (<1%). Additionally, the environmental friendliness catalyst could be retrieved through simple centrifugation within a few cycles. This study also offers a new pathway for the application of such biopolymer surface functionalization in organic transformations.

CAS / MDL: 9004-62-0
研究领域: 化学 · 材料科学 · 环境科学
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CELLULOSE · 2023 ·Vol. 30 ·期 16 ·10243-10255 · IF 5.7

Regenerated cellulose supported palladium composite superfine fibers as an efficient and recyclable catalyst for Suzuki reaction

Liu Yaqing,Zhang Xi,Huang Xudong,Shao Linjun,Xing Guiying,Qi Chenze,Zhou Shujing,Li Jinjing

Palladium cation embedded cellulose acetate/poly(vinyl butyral) composite superfine fibers were successfully fabricated by electrospinning. Then, these composite fibers were treated with hydrazine hydrate/NaOH/ethanol solution to regenerate cellulose from cellulose acetate and poly(vinyl alcohol) from poly(vinyl butyral). Meanwhile, the Pd 2+ cations were reduced to Pd 0 nanoparticles, which were evenly dispersed inside the fibers. The catalytic performance of these embedded Pd 0 nanoparticles were evaluated by Suzuki reaction. The catalysis results show that this novel fibrous catalyst was highly active to catalyze the Suzuki reaction of aromatic iodides and bromides with yields over 90%. Moreover, this fibrous palladium catalyst could be readily recovered and reused for 15 times with little loss of initial catalytic activity. The high catalytic activity can be ascribed to the superfine diameter of fibers while the excellent recyclability can be attributed to the embedment of active palladium species inside the fibers. Therefore, we have developed a facile method to prepare highly active and stable cellulose supported palladium fibrous catalysts.

CAS / MDL: 9004-35-7 3375-31-3
研究领域: 材料科学 · 催化化学
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Materials Research Express · 2017 ·Vol. 4 ·期 7 ·075022 · IF 1.068

Efficient synthesis of PtPd/Fe3O4 nanoparticles and its magnetic recoverability and stable recyclability for the Heck and Suzuki reactions

Yuanxu Sun,Xiaoqing Zhu,Dandan Guo,Xiao Chen,Jingtao Dai

Platinum and palladium bimetal nanoparticles on ferroferric oxide (PtPd/Fe3O4 NPs) nanocomposite catalysts were successfully synthesized with polyvinyl pyrrolidone as a stabilizing agent. The resultant samples were characterized by x-ray diffraction, x-ray photoelectron spectroscopy, transmission electron microscopy, high-resolution transmission electron microscopy, inductively coupled plasma, and magnetic studies. The catalytic performance of the PtPd/Fe3O4 NPs in the Heck and Suzuki coupling reactions was evaluated. Results showed that the cubic phase of Pt and Pd bimetal nanoparticles coexists with that of Fe3O4. The PtPd/Fe3O4 NP catalysts, which were approximately 22 nm in size, showed excellent catalytic activity in the Heck and Suzuki reactions. Moreover, the catalyst can be recovered with a magnet and reused several times without the significant loss of catalytic activity.

研究领域: 材料科学 · 化学
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