Abstract
Direct C-H trifluoromethylation of arenes and heteroarenes poses an important synthetic challenge that is highly desirable. High-valent CuIII -CF3 compounds have often been invoked in copper-mediated trifluoromethylation reactions, but the fundamental reactivity toward arenes is elusive. Herein, direct C-H trifluoromethylation of arenes/heteroarenes by a high-valent CuIII -CF3 compound is disclosed for the first time. The CuIII -CF3 compound serves CF3 radical and a CuII oxidant by homolytic cleavage of a CuIII -CF3 bond, which engage synergistically in a SE Ar type reaction with arenes. The presence of K2 S2 O8 co-oxidant can significantly improve the reaction yields. This reaction shows good efficiency, broad functional group tolerance, and the potential in late-stage functionalization. The reactivity of high-valent CuIII -CF3 compounds disclosed in this study represents an important progress in organofluorine and CuIII chemistry.
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