{"title":"<i>Meta</i>-, Regioselective Amination of Cyclic Diaryliodoniums through C-I and C-O Bond Cleavages: An Access to Functionalized Coumarins.","authors":"Jiadi Li, Bingling Luo, Peisen Huang, Yameng Sun, Peng Huang, Shijun Wen, Daqian Zhu","doi":"10.1021/acs.joc.4c02094","DOIUrl":null,"url":null,"abstract":"<p><p>Despite the widespread <i>ortho</i>-functionalization of cyclic diaryliodoniums in organic chemistry, the corresponding <i>meta</i>-functionalization is less explored. Herein, we report a practical <i>meta</i>-selective activation of cyclic hypervalent iodoniums for the synthesis of 4-amino coumarin derivatives in a broad functional group tolerance and environmentally friendly manner. The practicability of this protocol was further highlighted by the late-stage modification of some common pharmaceuticals and natural products.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":"3128-3139"},"PeriodicalIF":3.3000,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02094","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/2/26 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Despite the widespread ortho-functionalization of cyclic diaryliodoniums in organic chemistry, the corresponding meta-functionalization is less explored. Herein, we report a practical meta-selective activation of cyclic hypervalent iodoniums for the synthesis of 4-amino coumarin derivatives in a broad functional group tolerance and environmentally friendly manner. The practicability of this protocol was further highlighted by the late-stage modification of some common pharmaceuticals and natural products.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.