{"title":"Practical cuprous catalyzed anti-Markovnikov difluoroacetamidation of α-(trifluoromethyl)styrenes","authors":"Qian-Ding Zeng, Hongmiao Yao, Xinxin Yuan, Jian Wang, Bu-Bing Zeng, Jiangmeng Ren, Wu-Lin Yang","doi":"10.1016/j.tetlet.2024.155310","DOIUrl":null,"url":null,"abstract":"<div><div>An anti-Markovnikov difluoroacetamidation of α-(trifluoromethyl)styrenes was successfully performed, yielding 2,2,5,5,5-pentafluoropentanamides in good yields. This reaction was catalyzed by CuBr in the presence of pentamethyldiethylenetriamine (PMDETA) in MeCN, conducted under a nitrogen atmosphere. To assess the influence of substituent groups on the aromatic ring, two series of substrates were tested within the developed catalytic system. Additionally, scale-up applications and mechanistic studies were carried out.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"151 ","pages":"Article 155310"},"PeriodicalIF":1.5000,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004052","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/10/5 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
An anti-Markovnikov difluoroacetamidation of α-(trifluoromethyl)styrenes was successfully performed, yielding 2,2,5,5,5-pentafluoropentanamides in good yields. This reaction was catalyzed by CuBr in the presence of pentamethyldiethylenetriamine (PMDETA) in MeCN, conducted under a nitrogen atmosphere. To assess the influence of substituent groups on the aromatic ring, two series of substrates were tested within the developed catalytic system. Additionally, scale-up applications and mechanistic studies were carried out.
期刊介绍：
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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