{"title":"钯催化级联远端 C-H 甲基化和环化以构建螺吲哚骨架","authors":"Feng Wei, Yanghui Zhang","doi":"10.1021/acs.orglett.4c03315","DOIUrl":null,"url":null,"abstract":"Transition metal-catalyzed C–H methylation represents a straightforward approach for introducing methyl groups into organic molecules. Herein, we report a palladium-catalyzed alkene-relayed remote C–H methylation reaction that utilizes dimethyl carbonate as the methylation reagent. The aryl groups distal to a bromo group were dimethylated via C–H activation, leading to the formation of spirooxindoles as the final products through C(sp<sup>3</sup>)–H activation and C(sp<sup>3</sup>)–C(sp<sup>3</sup>) coupling. This cascade process involves the formation of four C–C bonds and the activation of three C–H bonds. The reaction not only provides a new approach to C–H methylation but also offers a novel method for constructing spirooxindole skeletons by merging skeleton construction and methylation into a single step.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium-Catalyzed Cascade Distal C–H Methylation and Cyclization for the Construction of Spirooxindole Skeletons\",\"authors\":\"Feng Wei, Yanghui Zhang\",\"doi\":\"10.1021/acs.orglett.4c03315\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Transition metal-catalyzed C–H methylation represents a straightforward approach for introducing methyl groups into organic molecules. Herein, we report a palladium-catalyzed alkene-relayed remote C–H methylation reaction that utilizes dimethyl carbonate as the methylation reagent. The aryl groups distal to a bromo group were dimethylated via C–H activation, leading to the formation of spirooxindoles as the final products through C(sp<sup>3</sup>)–H activation and C(sp<sup>3</sup>)–C(sp<sup>3</sup>) coupling. This cascade process involves the formation of four C–C bonds and the activation of three C–H bonds. The reaction not only provides a new approach to C–H methylation but also offers a novel method for constructing spirooxindole skeletons by merging skeleton construction and methylation into a single step.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2024-10-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.4c03315\",\"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://doi.org/10.1021/acs.orglett.4c03315","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 Cascade Distal C–H Methylation and Cyclization for the Construction of Spirooxindole Skeletons
Transition metal-catalyzed C–H methylation represents a straightforward approach for introducing methyl groups into organic molecules. Herein, we report a palladium-catalyzed alkene-relayed remote C–H methylation reaction that utilizes dimethyl carbonate as the methylation reagent. The aryl groups distal to a bromo group were dimethylated via C–H activation, leading to the formation of spirooxindoles as the final products through C(sp3)–H activation and C(sp3)–C(sp3) coupling. This cascade process involves the formation of four C–C bonds and the activation of three C–H bonds. The reaction not only provides a new approach to C–H methylation but also offers a novel method for constructing spirooxindole skeletons by merging skeleton construction and methylation into a single step.
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.