{"title":"Iron-Catalyzed Dearomatizing Reductive Cyclization of Arenes.","authors":"Ling-Jie Song, Xiao-Dong Zhang, Zheng-Hao Jin, Ren-Xiao Liang, Yi-Xia Jia","doi":"10.1021/acs.orglett.4c04680","DOIUrl":null,"url":null,"abstract":"<p><p>An efficient iron-catalyzed intramolecular dearomatizing reductive cyclization of arenes has been developed. By employing FeBr<sub>2</sub> as the catalyst, tripyridine as the ligand, and Mn powder as the reductant, a series of spiro-cyclohexadienes and dihydronaphthalenes were afforded in moderate to excellent yields with aryliodine-tethered benzyl <i>tert</i>-butyl carbonate or naphthalene derivatives as substrates. In addition, several synthetic transformations were conducted to demonstrate the utility of the reaction, and control experiments were carried out to gain insight into the mechanism.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"1390-1395"},"PeriodicalIF":5.0000,"publicationDate":"2025-02-14","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.4c04680","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/31 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
An efficient iron-catalyzed intramolecular dearomatizing reductive cyclization of arenes has been developed. By employing FeBr2 as the catalyst, tripyridine as the ligand, and Mn powder as the reductant, a series of spiro-cyclohexadienes and dihydronaphthalenes were afforded in moderate to excellent yields with aryliodine-tethered benzyl tert-butyl carbonate or naphthalene derivatives as substrates. In addition, several synthetic transformations were conducted to demonstrate the utility of the reaction, and control experiments were carried out to gain insight into the mechanism.
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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