Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes

作者：Youai Qiu, Alexej Scheremetjew, Lars H. Finger, Lutz Ackermann · 发表于：Chemistry - A European Journal · 年份：2019 · DOI：10.1002/chem.201905774 · 被引用次数：202 · 研究领域：Fluorine in Organic Chemistry、Radical Photochemical Reactions、Sulfur-Based Synthesis Techniques

Abstract Electrophotochemistry has enabled arene C−H trifluoromethylation with the Langlois reagent CF 3 SO 2 Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant‐free approach for the generation of the CF 3 radical. The electrophotochemistry was carried out in an operationally simple manner, setting the stage for challenging C−H trifluoromethylations of unactivated arenes and heteroarenes. The robust nature of the electrophotochemical manifold was reflected by a wide scope, including electron‐rich and electron‐deficient benzenes, as well as naturally occurring heteroarenes. Electrophotochemical C−H trifluoromethylation was further achieved in flow with a modular electro‐flow‐cell equipped with an in‐operando monitoring unit for on‐line flow‐NMR spectroscopy, providing support for the single electron transfer processes.