{"title":"钯催化硼酸甘酯与芳基硫铵盐的Suzuki-Miyaura偶联合成c -芳基甘酯。","authors":"Yu Zhang, , , Chengyang Guan, , , Mingjie Zeng, , , Qian Wang, , , Hong Liu*, , and , Jiang Wang*, ","doi":"10.1021/acs.orglett.5c03390","DOIUrl":null,"url":null,"abstract":"<p >Aryl <i>C</i>-glycosides represent key structure motifs in numerous natural products and pharmaceuticals. Here, we report a palladium-catalyzed Suzuki–Miyaura cross-coupling reaction between glycal boronates and aryl thianthrenium salts under mild conditions, enabling the synthesis of <i>C</i>-aryl glycals. This method features broad substrate scope, excellent functional group tolerance, and operational simplicity. Furthermore, the synthetic utility of this strategy is demonstrated through late-stage functionalization of structurally complex drug molecules, underscoring its potential for medicinal chemistry applications.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 38","pages":"10778–10784"},"PeriodicalIF":5.0000,"publicationDate":"2025-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium-Catalyzed Suzuki–Miyaura Couplings of Glycal Boronates with Aryl Thianthrenium Salts for the Synthesis of C-Aryl Glycals\",\"authors\":\"Yu Zhang, , , Chengyang Guan, , , Mingjie Zeng, , , Qian Wang, , , Hong Liu*, , and , Jiang Wang*, \",\"doi\":\"10.1021/acs.orglett.5c03390\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Aryl <i>C</i>-glycosides represent key structure motifs in numerous natural products and pharmaceuticals. Here, we report a palladium-catalyzed Suzuki–Miyaura cross-coupling reaction between glycal boronates and aryl thianthrenium salts under mild conditions, enabling the synthesis of <i>C</i>-aryl glycals. This method features broad substrate scope, excellent functional group tolerance, and operational simplicity. Furthermore, the synthetic utility of this strategy is demonstrated through late-stage functionalization of structurally complex drug molecules, underscoring its potential for medicinal chemistry applications.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 38\",\"pages\":\"10778–10784\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-09-17\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03390\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03390","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Palladium-Catalyzed Suzuki–Miyaura Couplings of Glycal Boronates with Aryl Thianthrenium Salts for the Synthesis of C-Aryl Glycals
Aryl C-glycosides represent key structure motifs in numerous natural products and pharmaceuticals. Here, we report a palladium-catalyzed Suzuki–Miyaura cross-coupling reaction between glycal boronates and aryl thianthrenium salts under mild conditions, enabling the synthesis of C-aryl glycals. This method features broad substrate scope, excellent functional group tolerance, and operational simplicity. Furthermore, the synthetic utility of this strategy is demonstrated through late-stage functionalization of structurally complex drug molecules, underscoring its potential for medicinal chemistry applications.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.