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用于叠氮化物-炔烃环加成反应的铜基固体多相催化剂的最新进展

Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide-Alkyne Cycloaddition Reactions.

作者信息

Aflak Noura, Ben El Ayouchia Hicham, Bahsis Lahoucine, Anane Hafid, Julve Miguel, Stiriba Salah-Eddine

机构信息

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

Laboratoire de Chimie de Coordination et d'Analytique/LCCA, Département de Chimie, Faculté des Sciences d'El Jadida, Université Chouaïb Doukkali, El Jadida 24000, Morocco.

出版信息

Int J Mol Sci. 2022 Feb 21;23(4):2383. doi: 10.3390/ijms23042383.

Abstract

The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction is considered to be the most representative ligation process within the context of the "click chemistry" concept. This CuAAC reaction, which yields compounds containing a 1,2,3-triazole core, has become relevant in the construction of biologically complex systems, bioconjugation strategies, and supramolecular and material sciences. Although many CuAAC reactions are performed under homogenous conditions, heterogenous copper-based catalytic systems are gaining exponential interest, relying on the easy removal, recovery, and reusability of catalytically copper species. The present review covers the most recently developed copper-containing heterogenous solid catalytic systems that use solid inorganic/organic hybrid supports, and which have been used in promoting CuAAC reactions. Due to the demand for 1,2,3-triazoles as non-classical bioisosteres and as framework-based drugs, the CuAAC reaction promoted by solid heterogenous catalysts has greatly improved the recovery and removal of copper species, usually by simple filtration. In so doing, the solving of the toxicity issue regarding copper particles in compounds of biological interest has been achieved. This protocol is also expected to produce a practical chemical process for accessing such compounds on an industrial scale.

摘要

铜(I)催化的叠氮化物-炔烃环加成(CuAAC)反应被认为是“点击化学”概念中最具代表性的连接过程。这种生成含有1,2,3-三唑核心化合物的CuAAC反应,在构建生物复杂体系、生物共轭策略以及超分子和材料科学中变得至关重要。尽管许多CuAAC反应是在均相条件下进行的,但基于铜的多相催化体系正受到越来越多的关注,这依赖于催化活性铜物种易于去除、回收和重复使用的特性。本综述涵盖了最近开发的含铜多相固体催化体系,这些体系使用固体无机/有机杂化载体,并已用于促进CuAAC反应。由于对作为非经典生物电子等排体和骨架型药物的1,2,3-三唑有需求,固体多相催化剂促进的CuAAC反应极大地改善了铜物种的回收和去除,通常通过简单过滤即可实现。这样一来,就解决了生物活性化合物中铜颗粒的毒性问题。该方案还有望产生一种实用的化学方法,以便在工业规模上制备此类化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c7fb/8874673/119ea3fc67ef/ijms-23-02383-sch001.jpg

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