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首页> 外文期刊>RSC Advances >Cu(ii)-alginate-based superporous hydrogel catalyst for click chemistry azide-alkyne cycloaddition type reactions in water
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Cu(ii)-alginate-based superporous hydrogel catalyst for click chemistry azide-alkyne cycloaddition type reactions in water

机译：Cu（II） - 基于氨基酸的过孔水凝胶催化剂，用于点击水中的化学叠氮化物 - 炔烃环加入型反应

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摘要

A novel sustainable hydrogel catalyst based on the reaction of sodium alginate naturally extracted from brown algaeLaminaria digitataresidue with copper(ii) was prepared as spherical beads, namely Cu(ii)-alginate hydrogel (Cu(ii)-AHG). The morphology and structural characteristics of these beads were elucidated by different techniques such as SEM, EDX, BET, FTIR and TGA analysis. Cu(ii)-AHG and its dried form, namely Cu(ii)-alginate (Cu(ii)-AD), are relatively uniform with an average pore ranging from 200 nm to more than 20 mu m. These superporous structure beads were employed for the copper catalyzed [3 + 2] cycloaddition reaction of aryl azides and terminal aryl alkynes (CuAAC)viaclick chemistry at low catalyst loading, using water as a solvent at room temperature and pressure. The catalytic active copper(i) species was generated by the reduction of copper(ii) by terminal alkyneviathe oxidative alkyne homocoupling reaction. The prepared catalysts were found to be efficient (85-92%) and regioselective by affording only 1,4-disubstituted-1,2,3-triazoles. They were also recoverable and reused in their dried form for at least four consecutive times without a clear loss of efficiency. A mechanistic study was performed through density functional theory (DFT) calculations in order to explain the regioselectivity outcome of Cu(ii)-alginate in CuAAC reactions. The analysis of the local electrophilicity (omega(k)) at the electrophilic reagent and the local nucleophilicity (N-k) at the nucleophilic confirms the polar character of CuAAC. This catalyst has the main advantage of being sustainably ligand-free and recyclable.
机译：制备基于藻酸钠的反应的新型可持续水凝胶催化剂用铜（II）天然萃取，作为球形珠，即Cu（II） - 丙氨酸水凝胶（Cu（II）-Ahg）。通过不同的技术（如SEM，EDX，BET，FTIR和TGA分析）阐明了这些珠子的形态和结构特征。 -AHG及其干燥的形式，即Cu（II） - 丙酸盐（Cu（II）-AD），相对均匀，平均孔径为200nm至超过20μm。这些高型结构珠子用于芳基含氮和末端芳基炔（Cuaac）的铜催化[3 + 2]环加成反应在低催化剂负载下在室温和压力下用水作为溶剂。催化活性铜（I）物种通过烷烷炔烃末端的铜（II）的氧化性炔烃同性耦合反应而产生。发现制备的催化剂通过仅提供1,4-二取代的-1,2,3-三唑来高效（85-92％）和区域选择性。它们也被恢复并连续四次以干燥的形式重复使用，而不会明确损失效率。通过密度泛函理论（DFT）计算进行机械研究，以解释Cu（II）的分区域结果 - 在CUAAC反应中进行丙氨酸。亲电试剂和局部亲核（N-K）的局部电泳（OMEGA（k））分析在亲核的证实CUAAC的极性特征。该催化剂具有可持续配体和可回收的主要优点。

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  • 来源
    《RSC Advances》 |2020年第54期|共12页
  • 作者

    Bahsis Lahoucine; Ablouh El-Houssaine; Anane Hafid; Taourirte Moha; Julve Miguel; Stiriba Salah-Eddine;

  • 作者单位

    Univ Chouaib Doukkali Fac Sci El Jadida Dept Chim BP 20 El Jadida 24000 Morocco;

    Univ Cadi Ayyad Fac Sci &

    Tech Marrakech Lab Chim Bioorgan &

    Macromol Marrakech 40000 Morocco;

    Univ Cadi Ayyad Fac Polydisciplinaire Safi Lab Chim Analyt &

    Mol LCAM Safi 4162 Morocco;

    Univ Cadi Ayyad Fac Sci &

    Tech Marrakech Lab Chim Bioorgan &

    Macromol Marrakech 40000 Morocco;

    Univ Valencia Inst Ciencia Mol ICMol Valencia 46980 Spain;

    Univ Cadi Ayyad Fac Polydisciplinaire Safi Lab Chim Analyt &

    Mol LCAM Safi 4162 Morocco;

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  • 正文语种 eng
  • 中图分类 化学;
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