{"title":"Iron-Catalyzed Perfluoroalkylarylation of Styrenes with Arenes and Alkyl Iodides Enabled by Halogen Atom Transfer.","authors":"Han-Qing Zhao, Wan-Ting Li, Yong Yao, Yi-Lin Zhao, Xuan-Hui Ouyang","doi":"10.1021/acs.orglett.4c04095","DOIUrl":null,"url":null,"abstract":"<p><p>A new iron-catalyzed three-component perfluoroalkylarylation of styrenes with alkyl halides and arenes has been established. Alkyl halides undergo halogen atom transfer with methyl radicals to form alkyl radicals in reactions initiated by a combination of <i>tert</i>-butyl peroxybenzoate and an iron catalyst, thus adducting to the olefins, which results in alkylarylation products. The protocol is compatible with a wide range of perfluoroalkyl and non-perfluoroalkyl halides, features excellent functional group tolerance, and enables the synthesis of structurally diverse 1,1-diaryl fluoro-substituted alkanes.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"10183-10188"},"PeriodicalIF":5.0000,"publicationDate":"2024-11-29","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.4c04095","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/11/18 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A new iron-catalyzed three-component perfluoroalkylarylation of styrenes with alkyl halides and arenes has been established. Alkyl halides undergo halogen atom transfer with methyl radicals to form alkyl radicals in reactions initiated by a combination of tert-butyl peroxybenzoate and an iron catalyst, thus adducting to the olefins, which results in alkylarylation products. The protocol is compatible with a wide range of perfluoroalkyl and non-perfluoroalkyl halides, features excellent functional group tolerance, and enables the synthesis of structurally diverse 1,1-diaryl fluoro-substituted alkanes.
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.
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