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新型 Huisgen 反应研究进展:多相铜催化叠氮-炔环加成反应合成 1,4-二取代三唑(综述,2018-2023)。

A New Insight Into The Huisgen Reaction: Heterogeneous Copper Catalyzed Azide-Alkyne Cycloaddition for the Synthesis of 1,4-Disubstituted Triazole (From 2018-2023).

机构信息

Department of Pharmaceutical Chemistry, ISF College of Pharmacy, Moga, 142001, Punjab, India.

Department of Pharmaceutics, ISF College of Pharmacy, Moga, 142001, Punjab, India.

出版信息

Chem Biodivers. 2024 Jun;21(6):e202400109. doi: 10.1002/cbdv.202400109. Epub 2024 May 22.

DOI:10.1002/cbdv.202400109
PMID:38640439
Abstract

The Huisgen cycloaddition, often referred to as 1,3-Dipolar cycloaddition, is a well-established method for synthesizing 1,4-disubstituted triazoles. Originally conducted under thermal conditions [3+2] cycloaddition reactions were limited by temperature, prolonged reaction time, and regioselectivity. The introduction of copper catalyzed azide-alkyne cycloaddition (CuAAC) revitalized interest, giving rise to the concept of "click chemistry". The CuAAC has emerged as a prominent method for producing 1,2,3-triazole with excellent yields and exceptional regioselectivity even in unfavorable conditions. Copper catalysts conventionally facilitate azide-alkyne cycloadditions, but challenges include instability and recycling issues. In recent years, there has been a growing demand for heterogeneous and porous catalysts in various chemical reactions. Chemists have been more interested in heterogenous catalysts as a result of the difficulties in separating homogenous catalysts from reaction products. These catalysts are favored for their abundant active sites, extensive surface area, easy separation from reaction mixtures, and the ability to be reused. Heterogeneous catalysts have garnered significant attention due to their broad industrial utility, characterized by cost-effectiveness, stability, resistance to thermal degradation, and ease of removal compared to their homogeneous counterparts. The present review covers recent advancements from year 2018 to 2023 in the field of click reactions for obtaining 1,2,3-triazoles through Cu catalyzed 1,3-dipolar azide-alkyne cycloaddition and the properties of the catalyst, reaction conditions such as solvent, temperature, reaction time, and the impact of different heterogeneous copper catalysts on product yield.

摘要

Huisgen 环加成反应,通常称为 1,3-偶极环加成反应,是合成 1,4-取代三唑的一种成熟方法。最初在热条件下进行的 [3+2]环加成反应受到温度、反应时间和区域选择性的限制。铜催化的叠氮-炔环加成反应 (CuAAC) 的引入重新引起了人们的兴趣,产生了“点击化学”的概念。CuAAC 已成为一种卓越的方法,即使在不利条件下,也能以优异的产率和出色的区域选择性生成 1,2,3-三唑。铜催化剂通常促进叠氮-炔环加成反应,但存在稳定性和回收问题。近年来,各种化学反应对多相和多孔催化剂的需求不断增长。由于均相催化剂难以从反应产物中分离出来,化学家们对多相催化剂越来越感兴趣。这些催化剂因其丰富的活性位点、广泛的表面积、易于从反应混合物中分离以及可重复使用的特性而受到青睐。多相催化剂因其广泛的工业应用而备受关注,其特点是与均相催化剂相比具有成本效益、稳定性、抗热降解性和易于去除性。本综述涵盖了 2018 年至 2023 年期间点击反应领域的最新进展,通过 Cu 催化的 1,3-偶极叠氮-炔环加成反应获得 1,2,3-三唑以及催化剂的性质、反应条件(如溶剂、温度、反应时间)以及不同多相铜催化剂对产物产率的影响。

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