可见光诱导的无光催化剂自由基三氟甲基化反应
Visible-Light-Induced Photocatalyst-Free Radical Trifluoromethylation.
作者信息
Li Yufei, Liang Xin, Niu Kaikai, Gu Jun, Liu Fang, Xia Qing, Wang Qingmin, Zhang Weihua
机构信息
Jiangsu Key Laboratory of Pesticide Science, Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China.
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China.
出版信息
Org Lett. 2022 Aug 19;24(32):5918-5923. doi: 10.1021/acs.orglett.2c02150. Epub 2022 Aug 5.
An attractive, versatile, and operationally simple, visible-light-induced, transition-metal-free, photocatalyst-free, and oxidant-free trifluoromethylation has been demonstrated. Triflic anhydride (TfO), being inexpensive and readily available, was chosen as the radical trifluoromethyl source. Thianthrene was used as a recyclable TfO-activating reagent, and a high-yielding and scalable trifluoromethylation reaction was achieved. Density functional theory and mechanistic studies showed that a free radical homolytic process excited by visible light is involved in this reaction, generating a key trifluoromethyl radical intermediate.
已证明了一种具有吸引力、通用性强且操作简单的可见光诱导、无过渡金属、无光催化剂且无氧化剂的三氟甲基化反应。三氟甲磺酸酐（TfO）价格低廉且易于获得，被选为自由基三氟甲基源。噻蒽用作可循环使用的TfO活化试剂，实现了高产率且可扩展的三氟甲基化反应。密度泛函理论和机理研究表明，该反应涉及由可见光激发的自由基均裂过程，生成关键的三氟甲基自由基中间体。
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