Electrochemical Nitroindolylation Bifunctionalization Reaction of Arylalkenes

A novel electrochemical nitroindolylation bifunctionalization reaction of alkenes was developed. It was unprecedented that both C-C and C-N bonds were concurrently formed using sodium nitrite as the nitro free radical precursor in one pot. A series of α-aryl-β-nitroindole derivatives was generated in good to high yields. Moreover, a plausible mechanism for this bifunctionalization reaction of alkenes was proposed via a bromonitro intermediate in an SN2 pathway. In addition, ZCZ011, an expensive positive allosteric modulator of the cannabinoid CB1 receptor, was facilely synthesized using this method.