化学学报 ›› 2025, Vol. 83 ›› Issue (4): 354-359.DOI: 10.6023/A24110332 上一篇    下一篇

研究论文

草酰单胺配体促进的低剂量钯催化水相Suzuki偶联反应

杨雪a, 刘妍伶a, 陈霞b, 周晓玉b, 王爱玲a, 刘海龙b,*()   

  1. a 大连大学 环境与化学工程学院 大连 116622
    b 六盘水师范学院 化学与材料工程学院 六盘水 553004
  • 投稿日期:2024-11-01 发布日期:2024-12-16
  • 基金资助:
    贵州省自然科学基金(黔科合基础-ZK[2023]重点048); 贵州省教育厅基金(黔教技[2023]088); 高层次人才科研启动基金(LPSSY-KYJJ201909); 六盘水师范学院科研培育项目(LPSSYLPY202330); 贵州省煤炭清洁利用重点实验室(黔科合平台-人才[2020]2001); 六盘水师范学院科技创新团队(LPSSYKJTD201904)

Oxalyl Monoamide Ligand-Promoted Palladium-Catalyzed Suzuki Coupling Reactions in Aqueous Media at Low Doses

Xue Yanga, Yanling Liua, Xia Chenb, Xiaoyu Zhoub, Ailing Wanga, Hailong Liub()   

  1. a College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, China
    b School of Chemistry and Materials Engineering, Liupanshui Normal University, Liupanshui 553004, China
  • Received:2024-11-01 Published:2024-12-16
  • Contact: E-mail: hailongliu@lpssy.edu.cn
  • Supported by:
    Natural Science Foundation of Guizhou Province (qiankehejichu-ZK[2023]zhongdian048); Foundation of Guizhou Educational Committee (qianjiaoji [2023]088); High-level Talents Research Start-up Fund(LPSSY-KYJJ201909); Liupanshui Normal University Scientific Research and Cultivation Projects(LPSSYLPY202330); Guizhou Provincial Key Laboratory of Coal Clean Utilization (qiankehepingtai-rencai [2020]2001); Science and Technology Innovation Team at Liupanshui Normal University(LPSSYKJTD201904)

本工作报道了一种实用的低剂量钯催化Suzuki偶联反应体系, 该体系以简单的草酰单胺为配体, 在乙醇和水(体积比1∶2)组成的绿色溶剂体系中进行, 即使在底物与催化剂的物质的量比(n(S)/n(C))为70000∶1时, 也展现出优异的催化效率. 本研究证明了该反应体系对多种卤代杂芳基和芳基硼酸具有广泛的适用性, 并且产率优异. 同时拓展了草酰胺配体在催化反应中的适用范围.

关键词: Suzuki偶联, 酰胺配体, 水相合成, 低催化剂用量

A practical and environmentally friendly low-dose palladium-catalyzed Suzuki coupling reaction system, utilizing simple oxalyl monoamides as ligands is introduced in this work. The reaction is conducted in a green solvent system composed of ethanol and water in a volume ratio of 1∶2, which not only reduces the environmental impact but also enhances the solubility of the reactants. Even at a low catalyst loading of n(S)/n(C)=70000, this system demonstrates excellent catalytic efficiency, yielding outstanding product yields of up to 98%. This is a substantial improvement over traditional methods that require higher catalyst concentrations. The study demonstrates the broad applicability of this reaction system to a variety of halogenated heteroaryl and aryl boronic acids, which are common substrates in the synthesis of complex molecules and pharmaceuticals. The high and consistent yields from the reactions validate the system's reliability and robustness. This work not only provides a more sustainable approach to Suzuki-Miyaura Cross-Coupling (SMCC) but also broadens the utility of oxalyl monoamide ligands in catalysis, paving the way for further exploration and application in the field of homogeneous catalysis. In summary, the development of this low-dose palladium-catalyzed Suzuki coupling system with oxalyl monoamides as ligands offers a green and efficient alternative for the synthesis of biaryl compounds. The system's versatility and the high yields obtained underscore its potential for broader applications in organic synthesis and catalysis research. This work contributes significantly to the ongoing efforts to develop more sustainable and efficient catalytic processes in chemical synthesis, making it a valuable addition to the field of green chemistry and catalysis.

Key words: Suzuki coupling, amide ligand, aqueous media synthesis, low catalyst loading