{"title":"Substrate-Controlled Pentafluorosulfanylation of Activated Alkenes Containing the Benzimidazole Moiety with SF5Cl","authors":"Xinqiang Tan, Yuezhen Li, Shijie Liu, Ziyou Hao, Yingchang Guo, Ruiping Fan, Yunhui Yan, Jianmei Yuan, Lizhen Fang, Ping-Xin Zhou, Hao Tang, Yingling Wang","doi":"10.1021/acs.joc.5c00103","DOIUrl":null,"url":null,"abstract":"We report herein a method of substrate-controlled pentafluorosulfanylation of activated alkenes containing the benzimidazole moiety with SF<sub>5</sub>Cl, which provides a highly efficient way to access SF<sub>5</sub>-containing benzo[4,5]imidazole[2,1-<i>a</i>]isoquinolin-6(5<i>H</i>)-ones, as well as SF<sub>5</sub>-containing <i>N</i>-benzoyl benzimidazoles. Besides the pentafluorosulfanyl group (−SF<sub>5</sub>), the current method can be applied to the tetrafluorosulfanyl group (−SF<sub>4</sub>−) incorporation. A radical mechanism involving single electron transfer (SET) or the atom transfer radical addition (ATRA) process is proposed.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"6 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-04-14","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.5c00103","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
We report herein a method of substrate-controlled pentafluorosulfanylation of activated alkenes containing the benzimidazole moiety with SF5Cl, which provides a highly efficient way to access SF5-containing benzo[4,5]imidazole[2,1-a]isoquinolin-6(5H)-ones, as well as SF5-containing N-benzoyl benzimidazoles. Besides the pentafluorosulfanyl group (−SF5), the current method can be applied to the tetrafluorosulfanyl group (−SF4−) incorporation. A radical mechanism involving single electron transfer (SET) or the atom transfer radical addition (ATRA) process is proposed.
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.
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