Mn-Mediated Electrochemical Trifluoromethylation/C(sp<sup>2</sup>)–H Functionalization Cascade for the Synthesis of Azaheterocycles
Zhenxing ZhangDepartment of Energy and Resources Engineering, College of Engineering, Peking University, Beijing 100871, ChinaLei ZhangDepartment of Energy and Resources Engineering, College of Engineering, Peking University, Beijing 100871, ChinaYang CaoDepartment of Energy and Resources Engineering, College of Engineering, Peking University, Beijing 100871, ChinaFeng LiState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100871, ChinaGuangcan BaiState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100871, ChinaGuoquan LiuState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100871, ChinaYang YangDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United StatesFanyang MoDepartment of Energy and Resources Engineering, College of Engineering, Peking University, Beijing 100871, China
2019en
ABI
Аннотация
A general electrohemical strategy for the combined trifluoromethylation/C(sp2)–H functionalization using Langlois’ reagent as the CF3 source under oxidant-free conditions was developed. Using Mn salts as the redox mediator, this method provides an efficient and sustainable means to access a variety of functionalized heterocycles bearing a CF3 moiety. Detailed mechanistic studies are consistent with the formation of CF3-bound high oxidation state Mn species, suggesting a transition-metal-mediated CF3 transfer mechanism for this trifluoromethylation/C(sp2)–H functionalization process.
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