Shu-Kui Guo, Yu-Han Zhang, Fan Yang, Xiao-De An, Yao-Bin Shen, Jian Xiao* and Bin Qiu*,
{"title":"基于vqm的多样性导向合成策略合成所有环尺寸的中型杂环桥接双芳","authors":"Shu-Kui Guo, Yu-Han Zhang, Fan Yang, Xiao-De An, Yao-Bin Shen, Jian Xiao* and Bin Qiu*, ","doi":"10.1021/acs.orglett.5c0053110.1021/acs.orglett.5c00531","DOIUrl":null,"url":null,"abstract":"<p >Herein, for the first time, the controllable, accurate, and diverse synthesis of all ring sizes of medium-sized (8- to 11-membered) indole-derived bridged biaryls has been realized by using ingeniously designed <i>o</i>-alkynylnaphthols that feature cyclic amines with adjustable ring sizes. The transformation may proceed through a DBN-mediated in-situ generation of vinylidene <i>ortho</i>-quinone methides/indole-ring formation/ring expansion cascade sequence, which is characterized by acceptable to excellent yields and good functional group tolerance.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 13","pages":"3237–3241 3237–3241"},"PeriodicalIF":5.0000,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of All Ring Sizes of Medium-Sized Heterocycles Bridged Biaryls via VQM-Enabled Diversity-Oriented Synthetic Strategy\",\"authors\":\"Shu-Kui Guo, Yu-Han Zhang, Fan Yang, Xiao-De An, Yao-Bin Shen, Jian Xiao* and Bin Qiu*, \",\"doi\":\"10.1021/acs.orglett.5c0053110.1021/acs.orglett.5c00531\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Herein, for the first time, the controllable, accurate, and diverse synthesis of all ring sizes of medium-sized (8- to 11-membered) indole-derived bridged biaryls has been realized by using ingeniously designed <i>o</i>-alkynylnaphthols that feature cyclic amines with adjustable ring sizes. The transformation may proceed through a DBN-mediated in-situ generation of vinylidene <i>ortho</i>-quinone methides/indole-ring formation/ring expansion cascade sequence, which is characterized by acceptable to excellent yields and good functional group tolerance.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 13\",\"pages\":\"3237–3241 3237–3241\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-03-25\",\"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.5c00531\",\"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.5c00531","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Synthesis of All Ring Sizes of Medium-Sized Heterocycles Bridged Biaryls via VQM-Enabled Diversity-Oriented Synthetic Strategy
Herein, for the first time, the controllable, accurate, and diverse synthesis of all ring sizes of medium-sized (8- to 11-membered) indole-derived bridged biaryls has been realized by using ingeniously designed o-alkynylnaphthols that feature cyclic amines with adjustable ring sizes. The transformation may proceed through a DBN-mediated in-situ generation of vinylidene ortho-quinone methides/indole-ring formation/ring expansion cascade sequence, which is characterized by acceptable to excellent yields and good functional group tolerance.
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.