Catalyst-Free Hydroxytrifluoromethylation of Alkenes UsingIodotrifluoromethane
作者机构：College of Chemistry & Environment Protection EngineeringSouthwest Minzu UniversityChengduSichuan 610041China Key Laboratory of Organofluorine ChemistryShanghai Institute of Organic ChemistryChinese Academy of Sciencesand University of Chinese Academy of Sciences345 Lingling RoadShanghai 200032China Sanming Institute of Fluorochemical IndustrySanming UniversitySanmingFujian 365004China
出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)
年 卷 期：2019年第37卷第1期
页 面：597-604页
核心收录：
基 金：the National Natural Science Foundation of China (Nos.21672239,21737004 and 21421002) Key Laboratory of Photochemical Conversion and Optoelectr onic Materials,TIPC,CAS,the Sanming Institute of Fluorochemical Industry (Nos.FCIT201704GR,FCIT201705GR,FCIT201701BR) STS Program of Chinese Academy of Science (KF-STS-QYZX-068).
主 题：trifluoromethyl catalyst-free hydroxylation alkenes photochemistry
摘 要：The importance of CF3-containing molecules in pharmaceuticals, agrochemicals and materials intrigues the intense interest in synthetic methodology of these compounds. With a purpose to enrich trifluoromethylation methodology, we carefully examined the substrate scope of hydroxytrifluoromethylation of alkenes using iodotrifluoromethane, and the reaction provided β-trifluoromethyl alcohols in good yields under extremely mild conditions without catalysts. We found that our reaction can be applied to not only styrenes but also various aliphatic alkenes with excellent selectivity;no ketone was detected in most of our cases. Another feature of our discovery is “simple. The reaction was carried out in air, irradiated by visible light, at room temperature and most importantly no catalyst was needed. A solution of CF3I in DMSO was used as the facile trifluoromethylating reagent, which simplified the utilization of gaseous CF3I. Based on 19F NMR spectroscopy, we observed a halogen bond between CF3I and tertiary amine in this reaction. The interaction may promote single electron transfer by the visible light irradiation.
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