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醋酸纤维素负载铜作为一种高效可持续的非均相催化剂用于水相中的叠氮-炔环加成点击反应。

Cellulose Acetate-Supported Copper as an Efficient Sustainable Heterogenous Catalyst for Azide-Alkyne Cycloaddition Click Reactions in Water.

机构信息

Instituto de Ciencia Molecular/ICMol, Universidad de Valencia, C/Catedrático José Beltrán 2, 46980 Paterna, Valencia, Spain.

Laboratoire de Chimie Analytique et Moléculaire (LCAM), Faculté Polydisciplinaire de Safi, Université Cadi Ayyad, Safi 46030, Morocco.

出版信息

Int J Mol Sci. 2023 May 26;24(11):9301. doi: 10.3390/ijms24119301.

Abstract

A new sustainable heterogeneous catalyst for copper-catalyzed azide-alkyne cycloaddition reaction (CuAAC) was investigated. The preparation of the sustainable catalyst was carried out through the complexation reaction between the polysaccharide cellulose acetate backbone (CA) and copper(II) ions. The resulting complex [Cu(II)-CA] was fully characterized by using different spectroscopic methods such as Fourier-transform infrared spectroscopy (FTIR), Scanning Electron Microscopy (SEM), Energy Dispersive X-ray (EDX), Ultraviolet-visible (UV-vis), and Inductively Coupled Plasma (ICP) analyses. The Cu(II)-CA complex exhibits high activity in the CuAAC reaction for substituted alkynes and organic azides, leading to a selective synthesis of the corresponding 1,4-isomer 1,2,3-triazoles in water as a solvent and working at room temperature. It is worth noting that this catalyst has several advantages from the sustainable chemistry point of view including no use of additives, biopolymer support, reactions carried out in water at room temperature, and easy recovery of the catalyst. These characteristics make it a potential candidate not only for the CuAAC reaction but also for other catalytic organic reactions.

摘要

研究了一种用于铜催化叠氮-炔环加成反应(CuAAC)的新型可持续非均相催化剂。可持续催化剂的制备是通过多糖纤维素醋酸酯骨架(CA)与铜(II)离子之间的络合反应进行的。所得配合物[Cu(II)-CA]通过傅里叶变换红外光谱(FTIR)、扫描电子显微镜(SEM)、能谱(EDX)、紫外可见(UV-vis)和电感耦合等离子体(ICP)分析等不同光谱方法进行了充分表征。Cu(II)-CA 配合物在取代炔烃和有机叠氮化物的 CuAAC 反应中表现出高活性,导致在水作为溶剂和室温下反应时,选择性合成相应的 1,4-异构体 1,2,3-三唑。值得注意的是,从可持续化学的角度来看,该催化剂具有几个优点,包括不使用添加剂、生物聚合物载体、在室温下在水中进行反应以及催化剂易于回收。这些特性使其不仅成为 CuAAC 反应的潜在候选物,而且成为其他催化有机反应的潜在候选物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4141/10253314/254b90053c05/ijms-24-09301-sch001.jpg

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