Hai-Shan Jin, Yan Wang, Ru-Jie Zhang and Li-Ming Zhao*,
{"title":"Rh(III)催化3-芳基异吲哚酮与2-甲基三亚甲基碳酸酯通过C-H活化[3 + 4]环化制备异吲哚酮螺苯并西平","authors":"Hai-Shan Jin, Yan Wang, Ru-Jie Zhang and Li-Ming Zhao*, ","doi":"10.1021/acs.orglett.5c01573","DOIUrl":null,"url":null,"abstract":"<p >A Rh(III)-catalyzed C–H activation/annulation of 3-aryl-3-hydroxyisoindolinones with 2-methylidenetrimethylene carbonate has been developed. This method leads to the synthesis of seven-membered isoindolinone spirobenzoxepines through sequential C–C and C–O bond formations, which are interesting scaffolds in drug discovery. Its synthetic application has also been demonstrated to highlight the versatility. In addition, this is the first example in which 2-methylidenetrimethylene carbonate serves as a C3O1 synthon to accomplish [3 + 4] annulation in transition-metal-catalyzed C–H activation reactions.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 25","pages":"6611–6616"},"PeriodicalIF":5.0000,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Rh(III)-Catalyzed [3 + 4] Annulation of 3-Arylisoindolinones with 2-Methylidenetrimethylene Carbonate via C–H Activation to Access Isoindolinone Spirobenzoxepines\",\"authors\":\"Hai-Shan Jin, Yan Wang, Ru-Jie Zhang and Li-Ming Zhao*, \",\"doi\":\"10.1021/acs.orglett.5c01573\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >A Rh(III)-catalyzed C–H activation/annulation of 3-aryl-3-hydroxyisoindolinones with 2-methylidenetrimethylene carbonate has been developed. This method leads to the synthesis of seven-membered isoindolinone spirobenzoxepines through sequential C–C and C–O bond formations, which are interesting scaffolds in drug discovery. Its synthetic application has also been demonstrated to highlight the versatility. In addition, this is the first example in which 2-methylidenetrimethylene carbonate serves as a C3O1 synthon to accomplish [3 + 4] annulation in transition-metal-catalyzed C–H activation reactions.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 25\",\"pages\":\"6611–6616\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-06-13\",\"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.5c01573\",\"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.5c01573","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Rh(III)-Catalyzed [3 + 4] Annulation of 3-Arylisoindolinones with 2-Methylidenetrimethylene Carbonate via C–H Activation to Access Isoindolinone Spirobenzoxepines
A Rh(III)-catalyzed C–H activation/annulation of 3-aryl-3-hydroxyisoindolinones with 2-methylidenetrimethylene carbonate has been developed. This method leads to the synthesis of seven-membered isoindolinone spirobenzoxepines through sequential C–C and C–O bond formations, which are interesting scaffolds in drug discovery. Its synthetic application has also been demonstrated to highlight the versatility. In addition, this is the first example in which 2-methylidenetrimethylene carbonate serves as a C3O1 synthon to accomplish [3 + 4] annulation in transition-metal-catalyzed C–H activation reactions.
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.