{"title":"通过钯催化糖基化反应合成 C-糖苷","authors":"Wenli Tong , Jie-Ping Wan , Jianchao Liu","doi":"10.1039/d4qo01619j","DOIUrl":null,"url":null,"abstract":"<div><div> <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.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"11 23","pages":"Pages 6918-6941"},"PeriodicalIF":0.0000,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of C-glycosides enabled by palladium-catalyzed glycosylation reactions\",\"authors\":\"Wenli Tong , Jie-Ping Wan , Jianchao Liu\",\"doi\":\"10.1039/d4qo01619j\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div> <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.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"11 23\",\"pages\":\"Pages 6918-6941\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-10-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2052412924006946\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/10/15 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412924006946","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/10/15 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
Synthesis of C-glycosides enabled by palladium-catalyzed glycosylation reactions
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.