Qiaoya Zhang , Bifu Liu , Ci Chen , Yinling Li , Kejun Feng , Sheng Hu , Yang Gao , Yanping Huo , Qian Chen , Xianwei Li
{"title":"Regioselective C–H alkynylation with haloalkynes enabled by nitrogen functionalities via Rh catalysis†","authors":"Qiaoya Zhang , Bifu Liu , Ci Chen , Yinling Li , Kejun Feng , Sheng Hu , Yang Gao , Yanping Huo , Qian Chen , Xianwei Li","doi":"10.1039/d5qo00578g","DOIUrl":null,"url":null,"abstract":"<div><div>Regioselective introduction of the versatile alkyne functionality would enable rapid construction of molecular complexity; however, sterically hindered silyl-containing alkynylation reagents are typically required, thus, hampering further applications. Herein, we have developed a transformable nitrogen functionality-enabled regioselective C–H alkynylation cascade with aliphatic haloalkynes, furnishing alkynes and heterocycles, which thus facilitated concise synthesis of CB2 receptor agonist and protein kinase inhibitor analogues.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 18","pages":"Pages 4956-4962"},"PeriodicalIF":0.0000,"publicationDate":"2025-04-26","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/S2052412925003341","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Regioselective introduction of the versatile alkyne functionality would enable rapid construction of molecular complexity; however, sterically hindered silyl-containing alkynylation reagents are typically required, thus, hampering further applications. Herein, we have developed a transformable nitrogen functionality-enabled regioselective C–H alkynylation cascade with aliphatic haloalkynes, furnishing alkynes and heterocycles, which thus facilitated concise synthesis of CB2 receptor agonist and protein kinase inhibitor analogues.