Synthesis of 4-(Bromodifluoromethylseleno) Isocoumarins via Selenolation/Lactonization of 2-Alkynylbenzoates Enabled by a Multi-Component Reagents System
Dongxue Yin, Zhijian Wang, Kaiyue Yang, Yuli Sun, Dan Xiao, Xiaotong Wang, Yunfei Du
{"title":"Synthesis of 4-(Bromodifluoromethylseleno) Isocoumarins via Selenolation/Lactonization of 2-Alkynylbenzoates Enabled by a Multi-Component Reagents System","authors":"Dongxue Yin, Zhijian Wang, Kaiyue Yang, Yuli Sun, Dan Xiao, Xiaotong Wang, Yunfei Du","doi":"10.1021/acs.joc.4c02696","DOIUrl":null,"url":null,"abstract":"<i>p</i>-CF<sub>3</sub>BnSeCF<sub>2</sub>Br was developed as a bromodifluoromethylselenonating reagent, which was utilized by combining with <i>m</i>CPBA and Tf<sub>2</sub>O for the synthesis of 4-(bromodifluoromethylseleno) isocoumarins via the selenolation/lactonization of 2-alkynylbenzoates. The transformation was postulated to proceed via a multicomponent reagents system-enabled sequence involving the oxidation of <i>p</i>-CF<sub>3</sub>BnSeCF<sub>2</sub>Br by <i>m</i>CPBA into its selenium sulfoxide, activation of the generated sulfoxide by Tf<sub>2</sub>O into the electrophilic <i>p</i>-CF<sub>3</sub>BnSeOCF<sub>2</sub>Br salt, and selenolation/lactonization of 2-alkynylbenzoates by the reactive electrophilic species into 4-(bromodifluoromethylseleno) isocoumarins.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"109 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-01-25","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.4c02696","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
p-CF3BnSeCF2Br was developed as a bromodifluoromethylselenonating reagent, which was utilized by combining with mCPBA and Tf2O for the synthesis of 4-(bromodifluoromethylseleno) isocoumarins via the selenolation/lactonization of 2-alkynylbenzoates. The transformation was postulated to proceed via a multicomponent reagents system-enabled sequence involving the oxidation of p-CF3BnSeCF2Br by mCPBA into its selenium sulfoxide, activation of the generated sulfoxide by Tf2O into the electrophilic p-CF3BnSeOCF2Br salt, and selenolation/lactonization of 2-alkynylbenzoates by the reactive electrophilic species into 4-(bromodifluoromethylseleno) isocoumarins.
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.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
