{"title":"Iodopentafluorosulfanylation of [1.1.1]propellane and further functionalizations","authors":"Xin Zhao, Jia-Yi Shou, Feng-Ling Qing","doi":"10.1007/s11426-023-1715-2","DOIUrl":null,"url":null,"abstract":"<div><p>Pentafluorosulfanylated (SF<sub>5</sub>-) aromatics have shown great potential in drugs, and the bioisosteric replacement of aromatic ring with bicyclo[1.1.1]pentane (BCP) unit has attracted considerable attention recently. Consequently, pentafluorosulfanylated bicyclo[1.1.1]pentanes (SF<sub>5</sub>-BCPs) should have application in the realm of drug discovery. In this study, a one-pot iodopentafluorosulfanylation of [1.1.1]propellane with SF<sub>5</sub>Cl and CH<sub>2</sub>I<sub>2</sub> for the practical synthesis of iodopentafluorosulfanylated bicyclo[1.1.1]pentane (SF<sub>5</sub>-BCP-I) was developed. SF<sub>5</sub>-BCP-I was the first example of SF<sub>5</sub>-BCPs that could be transformed. The first general method to access SF<sub>5</sub>-substituted bicyclo[1.1.1]pentane derivatives was demonstrated through photoredox-catalyzed radical addition of SF<sub>5</sub>-BCP-I to alkenes and alkynes.</p><figure><div><div><div><picture><source><img></source></picture></div></div></div></figure></div>","PeriodicalId":772,"journal":{"name":"Science China Chemistry","volume":"66 10","pages":"2871 - 2877"},"PeriodicalIF":10.4000,"publicationDate":"2023-08-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Science China Chemistry","FirstCategoryId":"1","ListUrlMain":"https://link.springer.com/article/10.1007/s11426-023-1715-2","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Pentafluorosulfanylated (SF5-) aromatics have shown great potential in drugs, and the bioisosteric replacement of aromatic ring with bicyclo[1.1.1]pentane (BCP) unit has attracted considerable attention recently. Consequently, pentafluorosulfanylated bicyclo[1.1.1]pentanes (SF5-BCPs) should have application in the realm of drug discovery. In this study, a one-pot iodopentafluorosulfanylation of [1.1.1]propellane with SF5Cl and CH2I2 for the practical synthesis of iodopentafluorosulfanylated bicyclo[1.1.1]pentane (SF5-BCP-I) was developed. SF5-BCP-I was the first example of SF5-BCPs that could be transformed. The first general method to access SF5-substituted bicyclo[1.1.1]pentane derivatives was demonstrated through photoredox-catalyzed radical addition of SF5-BCP-I to alkenes and alkynes.
期刊介绍：
Science China Chemistry, co-sponsored by the Chinese Academy of Sciences and the National Natural Science Foundation of China and published by Science China Press, publishes high-quality original research in both basic and applied chemistry. Indexed by Science Citation Index, it is a premier academic journal in the field.
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