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.
Metal-Free Electrochemical Trifluoromethylation of Imidazole-Fused Heterocycles with Trifluoromethyl Thianthrenium Triflate
A novel and eco-friendly electrochemical activation of trifluoromethyl thianthrenium triflate (TT–CF 3 +OTf −) for trifluoromethylation of imidazole-fused heteroaromatic compounds was established. This method involves the direct electrolysis of TT–CF 3 +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
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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