{"title":"Palladium-catalyzed vinylation of indoles with vinyl ethers via deoxygenative coupling","authors":"Bowen Wang, Jianxiao Li, Wanqing Wu, Liangbin Huang, Huanfeng Jiang","doi":"10.1007/s11426-024-2184-x","DOIUrl":null,"url":null,"abstract":"<div><p>Indole is a promising heteroarene in many natural products and pharmaceuticals; therefore, various synthetic methods for indole functionalizations have arisen in recent years. Herein, we report a Pd-catalyzed deoxygenative coupling for the <i>N</i>-vinylation of indoles by employing vinyl ethers. The vinylated indoles could be readily prepared in good to excellent yields with N1-regioselectivity regardless of the electronic characteristics and substitution patterns of indole substrates. Some indole-based pharmaceutical molecules, such as gramine, evodiamine, rutaecarpine, and melatonine, are also successfully vinylated. Moreover, carbazoles and indazoles are shown to participate. Additionally, vinylated indole can readily transform into structurally interesting indole derivatives.\n</p><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":772,"journal":{"name":"Science China Chemistry","volume":"67 11","pages":"3785 - 3790"},"PeriodicalIF":10.4000,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Science China Chemistry","FirstCategoryId":"1","ListUrlMain":"https://link.springer.com/article/10.1007/s11426-024-2184-x","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Indole is a promising heteroarene in many natural products and pharmaceuticals; therefore, various synthetic methods for indole functionalizations have arisen in recent years. Herein, we report a Pd-catalyzed deoxygenative coupling for the N-vinylation of indoles by employing vinyl ethers. The vinylated indoles could be readily prepared in good to excellent yields with N1-regioselectivity regardless of the electronic characteristics and substitution patterns of indole substrates. Some indole-based pharmaceutical molecules, such as gramine, evodiamine, rutaecarpine, and melatonine, are also successfully vinylated. Moreover, carbazoles and indazoles are shown to participate. Additionally, vinylated indole can readily transform into structurally interesting indole derivatives.
期刊介绍：
Science China Chemistry, co-sponsored by the Chinese Academy of Sciences and the National Natural Science Foundation of China and published by Science China Press, publishes high-quality original research in both basic and applied chemistry. Indexed by Science Citation Index, it is a premier academic journal in the field.
Categories of articles include:
Highlights. Brief summaries and scholarly comments on recent research achievements in any field of chemistry.
Perspectives. Concise reports on thelatest chemistry trends of interest to scientists worldwide, including discussions of research breakthroughs and interpretations of important science and funding policies.
Reviews. In-depth summaries of representative results and achievements of the past 5–10 years in selected topics based on or closely related to the research expertise of the authors, providing a thorough assessment of the significance, current status, and future research directions of the field.
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