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1Catalyst-Free Hydroxytrifluoromethylation of Alkenes UsingIodotrifluoromethane显示文摘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.Zhaoben Su Yong Guo Qing-Yun Chen Zhi-Gang Zhao Bao-Yi Nian 2019Chinese Journal of Chemistry2019,37,6:4
2Copper-Catalyzed Benzylic C—H Functionalization, Oxidation and Cyclization of Methylarenes: Direct Access to z-Arylbenzothiazoles显示文摘Background and Originality Content As an inexpensive,fundamental and important feedstock for the petrochemical industry,methylarenes have long been regarded as one of the most widely used raw materials for a great variety of organic transformations.Therefore,the selective benzylic C(sp3)—H functionalization is particularly important,which provides a strategic means to utilize this resource.Wentao Yu Wanqing Wu Huanfeng Jiang 2019Chinese Journal of Chemistry2019,37,11:2
3External-Oxidant-Free Electrochemical Oxidative Trifluoromethylation of Arenes Using CF3SO2Na as the CF3 Source显示文摘Summary of main observation and conclusion An efficient and environmentally benign electrochemical oxidative radical C-H trifluoromethylation of arenes by employing Langlois reagent as the CF3 source was developed in this work.Neither transition metal catalysts nor external chemical oxidants were required in this trifluoromethylation process.The reaction could be conducted in gram scale with high reaction efficiency.Yong Deng Fangling Lu Siqi You Tianrui Xia Yifan Zheng Cuifen Lu Guichun Yang Zuxing Chen Meng Gao Aiwen Lei 2019Chinese Journal of Chemistry2019,37,8:0
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