A polystyrene–poly(ethylene glycol) (PS–PEG) resin-supported triazine-based polyethyleneamine dendrimer copper catalyst (PS–PEG-TD2–CuSO₄) was prepared and characterized by means of CP-MAS NMR, UV–vis/NIR, FTIR, SEM-EDX, XPS, and ICP-AES analyses. PS–PEG-TD2–CuSO₄ was highly active in the Huisgen 1,3-dipolar cycloaddition of various organic azides with alkynes in water as well as the three-component reaction of alkynes, alkyl bromides, and sodium azide under batch conditions to give the corresponding triazoles in excellent yields with high recyclability of the catalyst. TEM analysis suggested that the copper nanoparticles generated in situ through reduction of PS–PEG-TD2–CuSO₄ with sodium ascorbate serve as the active catalytic species. The application of PS–PEG-TD2–CuSO₄ catalyst in a continuous-flow Huisgen reaction for the synthesis of 1,2,3-triazoles was also examined. The cycloaddition of organic azides with alkynes was completed within 22 s in the continuous-flow system containing PS–PEG-TD2–CuSO₄ to give the corresponding triazoles in up to 99% yield. Moreover, the continuous-flow system accomplished the long-term continuous-flow cycloaddition for 48 h producing 10 g of a triazole as well as the successive flow reaction producing various kinds of triazoles.

中文翻译：

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两性树脂负载的三嗪基聚乙烯胺树状聚合物铜催化剂的间歇流和连续流惠氏剂1，3-偶极环加成反应

制备了聚苯乙烯-聚乙二醇（PS-PEG）树脂负载的三嗪基聚乙烯胺树状大分子铜催化剂（PS-PEG-TD2-CuSO ₄），并通过CP-MAS NMR，UV-vis / NIR进行了表征，FTIR，SEM-EDX，XPS和ICP-AES分析。PS-PEG-TD2-CuSO ₄在水中多种有机叠氮化物与炔烃的Huisgen 1,3-偶极环加成反应中以及在间歇条件下炔烃，烷基溴化物和叠氮化钠的三组分反应中具有很高的活性，从而得到相应的三唑，收率高，催化剂的回收率高。TEM分析表明，通过还原PS–PEG-TD2–CuSO ₄原位生成了铜纳米颗粒与抗坏血酸钠一起用作活性催化物质。还研究了PS-PEG-TD2-CuSO ₄催化剂在Huisgen连续流反应中合成1,2,3-三唑的应用。在包含PS-PEG-TD2-CuSO ₄的连续流系统中，有机叠氮化物与炔烃的环加成反应可在22 s内完成，从而以高达99％的收率得到相应的三唑。此外，连续流系统完成了48小时的长期连续流加成反应，生成了10 g三唑，以及连续流式反应生成了各种三唑。