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Metal-Free Electrochemical Trifluoromethylation of Imidazole-Fused Heterocycles with Trifluoromethyl Thianthrenium Triflate
Chang Ge, Lipeng Qiao, Yuyang Zhang, Kai Sun, Jiangzhen An, Mei Peng, Xiaolan Chen, Lingbo Qu, Bing Yu
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (15) : 1679-1685.
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Metal-Free Electrochemical Trifluoromethylation of Imidazole-Fused Heterocycles with Trifluoromethyl Thianthrenium Triflate
A novel and eco-friendly electrochemical activation of trifluoromethyl thianthrenium triflate (TT–CF3+OTf−) for trifluoromethylation of imidazole-fused heteroaromatic compounds was established. This method involves the direct electrolysis of TT–CF3+OTf− without the requirement of external oxidants or catalysts, aligning with the principles of green chemistry. A wide range of imidazole-fused heteroaromatic compounds including imidazo[1,2-a]pyridines and benzo[d]imidazo[2,1-b]thiazoles have been successfully trifluoromethylated using this technique, exhibiting excellent compatibility with various functional groups and a broad substrate scope. Moreover, the method's applicability for one-pot sequential reactions enables the reduction of waste and resource consumption by eliminating the need for intermediate purification steps.
Trifluoromethylation / Electrochemical / Metal-free / Imidazole-fused heterocycles / Thianthrenium
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