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A supramolecular recyclable catalyst for aqueous Suzuki-Miyaura coupling

机译:一种用于铃木 - Miyaura耦合水溶液的超分子可回收催化剂

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摘要

A water-soluble, supramolecular catalytic system has been designed based on inclusion complexation between a hydrophobic palladium(II)-dipyrazole complex bearing an adamantyl (Ad) molecular recognition moiety and a complementary, hydrophilic beta-cyclodextrin (beta-CD) derivative. The single-crystal molecular structure of the Pd(II) complex was determined and its host-guest inclusion complexation with heptakis(2,6-di-O-methyl)-beta-CD (dm beta-CD) in an aqueous medium was confirmed by 2D NOESY H-1 NMR spectroscopy. The catalyst showed high activity for Suzuki-Miyaura coupling of hydrophilic aryl bromides with aryl boronic acids in aqueous organic solvents. In the presence of n-Bu4NBr as a stabilizer, the catalyst-containing reaction solution can be recycled and reused multiple times to catalyze the coupling reaction of fresh substrates once the product has been removed by centrifugation. This work demonstrates a supramolecular complex approach, non-covalently modifying a water insoluble metal complex to provide a water-soluble inclusion system to serve as a recyclable catalyst for potential application in green chemical synthesis.
机译:基于含有金刚烷基(Ad)分子识别部分和互补的亲水性β-环糊精(β-CD)衍生物的疏水钯(II)-DiPyrazole复合物之间的包含络合而设计了一种水溶性的超分子催化系统。测定Pd(II)复合物的单晶分子结构,并在水性介质中与七(2,6-二-O-甲基)-beta-cd(DMβ-CD)的宿主 - 客剂包合物络合物由2D NOESY H-1 NMR光谱证实。催化剂对水性有机溶剂中芳基硼酸的亲水性芳基溴化物的铃木芳基溴化物偶联的高活性。在N-BU4NBR作为稳定剂的情况下,可以再循环含催化剂的反应溶液并重复使用,以催化新鲜基质的偶联反应一旦通过离心除去产物。该工作证明了一种超分子复杂的方法,非共价修饰水不溶性金属络合物,以提供水溶性包衣体系,用作可回收催化剂,用于在绿色化学合成中潜在应用。

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  • 来源
    《RSC Advances》 |2015年第5期|共7页
  • 作者单位

    ASTAR Inst Mat Res &

    Engn Singapore 117602 Singapore;

    ASTAR Inst Mat Res &

    Engn Singapore 117602 Singapore;

    ASTAR Inst Mat Res &

    Engn Singapore 117602 Singapore;

    ASTAR Inst Mat Res &

    Engn Singapore 117602 Singapore;

    ASTAR Inst Mat Res &

    Engn Singapore 117602 Singapore;

    ASTAR Inst Mat Res &

    Engn Singapore 117602 Singapore;

    ASTAR Inst Mat Res &

    Engn Singapore 117602 Singapore;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
  • 关键词

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