Practical Electrochemical Hydroxynitration and Chloronitration Bifunctionalization of Alkenes with NaNO2
Lingyan Liu1, Feng Zhang1, Xiangxi Liu1
1State Key Laboratory and Institute of Elemento-Organic Chemistry, National Engineering Research Center of Pesticide, Nankai University, College of Chemistry, Nankai University, Weijin Road 94#, Nankai District, Tianjin, 300071, P. R. China.
Abstract:
We herein developed a novel method for generating nitryl free radicals using sodium nitrite for the first time under electrocatalytic conditions. A series of vicinal hydroxynitro or chloronitro compounds was generated in good yields. This methodology features a simple reaction setup, mild reaction conditions, and cheap electrodes and shows excellent functional group tolerance and broad substrate scope, enabling efficient gram-scale reactions with good to excellent yields. Besides, the electrochemical impedance spectroscopy (EIS) and cyclic voltammetry (CV) results provided deeper insights into the reaction mechanism. Further extensions of the method have also confirmed the practicality of the strategy developed.
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