Samuel M G Dearman, Xiang Li, Yang Li, Kuldip Singh, Alison M Stuart
{"title":"使用 Selectfluor 进行氧化氟化：制备高价碘（V）氟化物的便捷程序。","authors":"Samuel M G Dearman, Xiang Li, Yang Li, Kuldip Singh, Alison M Stuart","doi":"10.3762/bjoc.20.157","DOIUrl":null,"url":null,"abstract":"<p><p>The ability to investigate hypervalent iodine(V) fluorides has been limited primarily by their difficult preparation traditionally using harsh fluorinating reagents such as trifluoromethyl hypofluorite and bromine trifluoride. Here, we report a mild and efficient route using Selectfluor to deliver hypervalent iodine(V) fluorides in good isolated yields (72-90%). Stability studies revealed that bicyclic difluoro(aryl)-λ<sup>5</sup>-iodane <b>6</b> was much more stable in acetonitrile-<i>d</i> <sub>3</sub> than in chloroform-<i>d</i> <sub>1</sub>, presumably due to acetonitrile coordinating to the iodine(V) centre and stabilising it via halogen bonding.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.2000,"publicationDate":"2024-07-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11301045/pdf/","citationCount":"0","resultStr":"{\"title\":\"Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides.\",\"authors\":\"Samuel M G Dearman, Xiang Li, Yang Li, Kuldip Singh, Alison M Stuart\",\"doi\":\"10.3762/bjoc.20.157\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>The ability to investigate hypervalent iodine(V) fluorides has been limited primarily by their difficult preparation traditionally using harsh fluorinating reagents such as trifluoromethyl hypofluorite and bromine trifluoride. Here, we report a mild and efficient route using Selectfluor to deliver hypervalent iodine(V) fluorides in good isolated yields (72-90%). Stability studies revealed that bicyclic difluoro(aryl)-λ<sup>5</sup>-iodane <b>6</b> was much more stable in acetonitrile-<i>d</i> <sub>3</sub> than in chloroform-<i>d</i> <sub>1</sub>, presumably due to acetonitrile coordinating to the iodine(V) centre and stabilising it via halogen bonding.</p>\",\"PeriodicalId\":8756,\"journal\":{\"name\":\"Beilstein Journal of Organic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.2000,\"publicationDate\":\"2024-07-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11301045/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Beilstein Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.3762/bjoc.20.157\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/1/1 0:00:00\",\"PubModel\":\"eCollection\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.20.157","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/1/1 0:00:00","PubModel":"eCollection","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides.
The ability to investigate hypervalent iodine(V) fluorides has been limited primarily by their difficult preparation traditionally using harsh fluorinating reagents such as trifluoromethyl hypofluorite and bromine trifluoride. Here, we report a mild and efficient route using Selectfluor to deliver hypervalent iodine(V) fluorides in good isolated yields (72-90%). Stability studies revealed that bicyclic difluoro(aryl)-λ5-iodane 6 was much more stable in acetonitrile-d3 than in chloroform-d1, presumably due to acetonitrile coordinating to the iodine(V) centre and stabilising it via halogen bonding.
期刊介绍：
The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry.
The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
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
