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Published on: June 20, 2014
Electrochemically Enabled C-H Arylation of Anilines
Zhenhua Li1,2, Fenghao Dai1, Lijun Chen1
1College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou310014, China.
None:
Electrochemistry enables the direct, mild generation of aryl radicals under metal-free conditions for the regioselective C-H arylation of anilines. This operationally simple protocol, which requires no external oxidant, employs an undivided cell and proceeds via direct anodic electron transfer at ambient temperature, delivering a range of functionalized N-heterocycles and medicinally relevant 2-aminobiphenyl scaffolds in moderate to good yields. Mechanistic studies, including kinetic isotope effects, radical-trapping experiments, and cyclic voltammetry, confirm an electrochemically driven radical pathway, wherein electron transfer serves as an alternative to conventional chemical oxidants and metal catalysts, enabling direct aryl radical formation and subsequent cross-coupling under mild electrochemical conditions.
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