{"title":"Synthesis of C-glycosides enabled by palladium-catalyzed glycosylation reactions","authors":"Wenli Tong, Jie-Ping Wan and Jianchao Liu","doi":"10.1039/D4QO01619J","DOIUrl":null,"url":null,"abstract":"<p >\r\n <em>C</em>-Glycosides are a privileged class of carbohydrates that exhibit remarkable biological and pharmaceutical activities. Transition metal-catalyzed cross-coupling reactions are powerful tools for the efficient and rapid construction of C–C bonds. Among various transition-metal catalyzed methods, palladium-catalyzed <em>C</em>-glycosylation is an effective and reliable approach to synthesize <em>C</em>-glycosides and involves the reaction of glycosyl donors and various reaction partners <em>via</em> C–C glycosidic bond formation under mild conditions with high regio/stereo-selectivities. In this review, palladium-catalyzed <em>C</em>-glycosylation reactions from 2020 to 2024 are summarized and discussed in detail, with focus on the synthesis of <em>C</em>-aryl glycosides, <em>C</em>-alkyl glycosides, <em>C</em>-alkenyl glycosides, and other functionalized <em>C</em>-glycosides. Some representative synthetic strategies and their transformation application along with reaction mechanisms are also highlighted.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":" 23","pages":" 6918-6941"},"PeriodicalIF":4.6000,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo01619j","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
C-Glycosides are a privileged class of carbohydrates that exhibit remarkable biological and pharmaceutical activities. Transition metal-catalyzed cross-coupling reactions are powerful tools for the efficient and rapid construction of C–C bonds. Among various transition-metal catalyzed methods, palladium-catalyzed C-glycosylation is an effective and reliable approach to synthesize C-glycosides and involves the reaction of glycosyl donors and various reaction partners via C–C glycosidic bond formation under mild conditions with high regio/stereo-selectivities. In this review, palladium-catalyzed C-glycosylation reactions from 2020 to 2024 are summarized and discussed in detail, with focus on the synthesis of C-aryl glycosides, C-alkyl glycosides, C-alkenyl glycosides, and other functionalized C-glycosides. Some representative synthetic strategies and their transformation application along with reaction mechanisms are also highlighted.
期刊介绍：
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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