Kun Yue, Ying Yuan, Haoyu Dong, Lu Wang, Bo Ren, Guiqin Lou, Jian Xiao
{"title":"含氮多齿配体与-NR3 +/ - PPh3+基团螯合Pd(0)纳米粒子功能化纤维,用于绿色催化C-C键偶联反应","authors":"Kun Yue, Ying Yuan, Haoyu Dong, Lu Wang, Bo Ren, Guiqin Lou, Jian Xiao","doi":"10.1016/j.tet.2025.134586","DOIUrl":null,"url":null,"abstract":"<div><div>Highly dispersion and small particle size Pd(0) nanoparticles were immobilized into nitrogen-containing polydentate ligand and quaternary ammonium/phosphonium salt bifunctionalized polyacrylonitrile fiber to prepared a novel functionalized fiber catalyst (PAN<sub>NP/QA&PS</sub>F-Pd(0)). Some necessary instrumental analysis methods, including inductively coupled plasma atomic emission spectroscopy (ICP-AES), X-ray photoelectron spectroscopy (XPS), Transmission Electron Microscope (TEM), etc., were applied to accurately characterize the microscopic physical and chemical properties of PAN<sub>NP/QA&PS</sub>F-Pd(0), confirming the structure of the novel fiber catalyst was in accordance with our expected design. Additionally, the Heck reaction was changed as a classic template reaction for evaluating the catalytic activity of prepared fiber catalyst. The result verified that PAN<sub>NP/QA&PS</sub>F-Pd(0) can efficiently catalyze the Heck reaction between different halogenated aromatic hydrocarbons and terminal olefins within 6 h under catalyst dosage of 0.02 % and solvent-free condition, and the isolated yields of target products can reach 46–99 %, respectively. Furthermore, PAN<sub>NP/QA&PS</sub>F-Pd(0) can also smoothly catalyze Suzuki reaction between different iodized aromatics and arylboric acids, achieving satisfactory yields of 67–99 %. Moreover, PAN<sub>NP/QA&PS</sub>F-Pd(0) can be reused 8 times with slight decline in catalytic activity (isolated yield of 91 % and 80 %, respectively), and the average size of Pd(0) nanoparticles only increased from 1.94 nm to 2.98 nm, verifing that the Pd(0) nanoparticles in PAN<sub>NP/QA&PS</sub>F-Pd(0) was validly dispersed and stabilized, which makes the fiber catalyst has excellent recyclability. Noteworthily, a reasonable heterogeneous catalytic mechanism was proposed.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134586"},"PeriodicalIF":2.2000,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Nitrogen-containing polydentate ligand with –NR3+/−PPh3+ moieties chelated Pd(0) nanoparticles functionalized fiber for green catalysis of C–C bond coupling reaction\",\"authors\":\"Kun Yue, Ying Yuan, Haoyu Dong, Lu Wang, Bo Ren, Guiqin Lou, Jian Xiao\",\"doi\":\"10.1016/j.tet.2025.134586\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Highly dispersion and small particle size Pd(0) nanoparticles were immobilized into nitrogen-containing polydentate ligand and quaternary ammonium/phosphonium salt bifunctionalized polyacrylonitrile fiber to prepared a novel functionalized fiber catalyst (PAN<sub>NP/QA&PS</sub>F-Pd(0)). Some necessary instrumental analysis methods, including inductively coupled plasma atomic emission spectroscopy (ICP-AES), X-ray photoelectron spectroscopy (XPS), Transmission Electron Microscope (TEM), etc., were applied to accurately characterize the microscopic physical and chemical properties of PAN<sub>NP/QA&PS</sub>F-Pd(0), confirming the structure of the novel fiber catalyst was in accordance with our expected design. Additionally, the Heck reaction was changed as a classic template reaction for evaluating the catalytic activity of prepared fiber catalyst. The result verified that PAN<sub>NP/QA&PS</sub>F-Pd(0) can efficiently catalyze the Heck reaction between different halogenated aromatic hydrocarbons and terminal olefins within 6 h under catalyst dosage of 0.02 % and solvent-free condition, and the isolated yields of target products can reach 46–99 %, respectively. Furthermore, PAN<sub>NP/QA&PS</sub>F-Pd(0) can also smoothly catalyze Suzuki reaction between different iodized aromatics and arylboric acids, achieving satisfactory yields of 67–99 %. Moreover, PAN<sub>NP/QA&PS</sub>F-Pd(0) can be reused 8 times with slight decline in catalytic activity (isolated yield of 91 % and 80 %, respectively), and the average size of Pd(0) nanoparticles only increased from 1.94 nm to 2.98 nm, verifing that the Pd(0) nanoparticles in PAN<sub>NP/QA&PS</sub>F-Pd(0) was validly dispersed and stabilized, which makes the fiber catalyst has excellent recyclability. Noteworthily, a reasonable heterogeneous catalytic mechanism was proposed.</div></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":\"177 \",\"pages\":\"Article 134586\"},\"PeriodicalIF\":2.2000,\"publicationDate\":\"2025-05-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040402025001425\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/3/11 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025001425","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/3/11 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Nitrogen-containing polydentate ligand with –NR3+/−PPh3+ moieties chelated Pd(0) nanoparticles functionalized fiber for green catalysis of C–C bond coupling reaction
Highly dispersion and small particle size Pd(0) nanoparticles were immobilized into nitrogen-containing polydentate ligand and quaternary ammonium/phosphonium salt bifunctionalized polyacrylonitrile fiber to prepared a novel functionalized fiber catalyst (PANNP/QA&PSF-Pd(0)). Some necessary instrumental analysis methods, including inductively coupled plasma atomic emission spectroscopy (ICP-AES), X-ray photoelectron spectroscopy (XPS), Transmission Electron Microscope (TEM), etc., were applied to accurately characterize the microscopic physical and chemical properties of PANNP/QA&PSF-Pd(0), confirming the structure of the novel fiber catalyst was in accordance with our expected design. Additionally, the Heck reaction was changed as a classic template reaction for evaluating the catalytic activity of prepared fiber catalyst. The result verified that PANNP/QA&PSF-Pd(0) can efficiently catalyze the Heck reaction between different halogenated aromatic hydrocarbons and terminal olefins within 6 h under catalyst dosage of 0.02 % and solvent-free condition, and the isolated yields of target products can reach 46–99 %, respectively. Furthermore, PANNP/QA&PSF-Pd(0) can also smoothly catalyze Suzuki reaction between different iodized aromatics and arylboric acids, achieving satisfactory yields of 67–99 %. Moreover, PANNP/QA&PSF-Pd(0) can be reused 8 times with slight decline in catalytic activity (isolated yield of 91 % and 80 %, respectively), and the average size of Pd(0) nanoparticles only increased from 1.94 nm to 2.98 nm, verifing that the Pd(0) nanoparticles in PANNP/QA&PSF-Pd(0) was validly dispersed and stabilized, which makes the fiber catalyst has excellent recyclability. Noteworthily, a reasonable heterogeneous catalytic mechanism was proposed.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.