Growing impact of ‘Click chemistry’ inspired glycohybrid 1,2,3-Triazoles in organic synthesis

IF 2.4 3区 化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY
Sumit K. Singh , Anindra Sharma , Nidhi Mishra , Vinod K. Tiwari
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Abstract

Carbohydrates, a most abundant natural product have fascinating structural features notably their high functional nature having multiple hydroxyl groups as well stereogenic centers which all together attracted the interest of synthetic chemists to explore them as valuable scaffolds in ligand design. In recent years, 1,2,3-triazole-linked sugar conjugates developed via regioselective CuAAC route have emerged as promising ligands in transition metal catalysis. These glycoconjugates have been applied in C–C and C–N bond-forming reactions, including Ullmann and Sonogashira couplings, particularly with Cu, Ni, and Pd catalysts. Their use has further extended to asymmetric catalysis, ligand-assisted activation, and sustainable synthesis. This review provides a concise overview of click-derived 1,2,3–triazole–sugar conjugates as promising ligands in transition metal catalysis, with highlighting their role in enhancing the catalytic reactivity, controlling the regio- and/or stereoselectivity, and improving the efficiency of metal-mediated transformations.
“Click化学”对1,2,3-三氮杂化糖在有机合成中的影响越来越大
碳水化合物是一种最丰富的天然产物,具有令人着迷的结构特征,特别是其具有多个羟基和立体中心的高功能特性,这些特性吸引了合成化学家的兴趣,将其作为配体设计中有价值的支架。近年来,通过区域选择性CuAAC途径开发的1,2,3-三唑糖缀合物已成为过渡金属催化中很有前途的配体。这些糖缀合物已应用于C-C和C-N成键反应,包括Ullmann和Sonogashira偶联,特别是与Cu, Ni和Pd催化剂。它们的用途已进一步扩展到不对称催化、配体辅助活化和可持续合成。本文综述了键衍生的1,2,3 -三唑-糖缀合物作为过渡金属催化中很有前途的配体,重点介绍了它们在增强催化活性、控制区域和/或立体选择性以及提高金属介导转化效率方面的作用。
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来源期刊
Carbohydrate Research
Carbohydrate Research 化学-生化与分子生物学
CiteScore
5.00
自引率
3.20%
发文量
183
审稿时长
3.6 weeks
期刊介绍: Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".
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