{"title":"gem-Difluorination of carbon–carbon triple bonds using Brønsted acid/Bu4NBF4 or electrogenerated acid","authors":"Mizuki Yamaguchi, Hiroki Shimao, Kengo Hamasaki, Keiji Nishiwaki, Shigenori Kashimura, Kouichi Matsumoto","doi":"10.3762/bjoc.20.194","DOIUrl":null,"url":null,"abstract":"<p><font size='+1'><b>Abstract</b></font></p>\n<p><i>gem</i>-Difluorination of carbon–carbon triple bonds was conducted using Brønsted acids, such as Tf<sub>2</sub>NH and TfOH, combined with Bu<sub>4</sub>NBF<sub>4</sub> as the fluorine source. The electrochemical oxidation of a Bu<sub>4</sub>NBF<sub>4</sub>/CH<sub>2</sub>Cl<sub>2</sub> solution containing alkyne substrates could also give the corresponding <i>gem</i>-difluorinated compounds (<i>in-cell</i> method). The <i>ex-cell</i> electrolysis method was also applicable for <i>gem</i>-difluorination of alkynes.</p>\n<p align='center'><img src='https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-20-194-graphical-abstract.png?max-width=550' border='0'/></p>\n<p><i>Beilstein J. Org. Chem.</i> <b>2024,</b> <i>20,</i> 2261–2269. doi:10.3762/bjoc.20.194</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"22 1","pages":""},"PeriodicalIF":2.2000,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.20.194","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
gem-Difluorination of carbon–carbon triple bonds was conducted using Brønsted acids, such as Tf2NH and TfOH, combined with Bu4NBF4 as the fluorine source. The electrochemical oxidation of a Bu4NBF4/CH2Cl2 solution containing alkyne substrates could also give the corresponding gem-difluorinated compounds (in-cell method). The ex-cell electrolysis method was also applicable for gem-difluorination of alkynes.
Beilstein J. Org. Chem.2024,20, 2261–2269. doi:10.3762/bjoc.20.194
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