光氧化还原催化剂介导的叔丁基芳基氨基甲酸酯的对位选择性三氟甲基化反应
Photoredox-Catalyst-Enabled para-Selective Trifluoromethylation of tert-Butyl Arylcarbamates.
作者信息
Jiang Yaqiqi, Li Bao, Ma Nana, Shu Sai, Chen Yujie, Yang Shan, Huang Zhibin, Shi Daqing, Zhao Yingsheng
机构信息
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, P. R. China.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453000, P. R. China.
出版信息
Angew Chem Int Ed Engl. 2021 Aug 23;60(35):19030-19034. doi: 10.1002/anie.202105631. Epub 2021 Jul 20.
The direct incorporation of a trifluoromethyl group on an aromatic ring using a radical pathway has been extensively investigated. However, the direct highly para-selective C-H trifluoromethylation of a class of arenes has not been achieved. In this study, we report a light-promoted 4,5-dichlorofluorescein (DCFS)-enabled para-selective C-H trifluoromethylation of arylcarbamates using Langlois reagent. The preliminary mechanistic study revealed that the activated organic photocatalyst coordinated with the arylcarbamate led to para-selective C-H trifluoromethylation. Ten-gram scale reaction performs well highlighting the synthetic importance of this new protocol.
利用自由基途径在芳环上直接引入三氟甲基已得到广泛研究。然而，一类芳烃的直接高对位选择性C-H三氟甲基化尚未实现。在本研究中，我们报道了一种光促进的、使用朗格卢瓦试剂实现芳基氨基甲酸酯的对位选择性C-H三氟甲基化的4,5-二氯荧光素（DCFS）方法。初步机理研究表明，活化的有机光催化剂与芳基氨基甲酸酯配位导致对位选择性C-H三氟甲基化。十克规模的反应表现良好，突出了这一新方法的合成重要性。
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