Benzylic C-H Arylation with Dicyanoarenes via Convergent Paired-Electrolysis

20 December 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


We describe the convergent paired electrolysis of methylarene derivatives and 1,4-dicyanoarenes to perform the arylative functionalization of a benzylic C(sp3)-H bond to form 1,1-biarylmethane derivatives which motif is found in several drugs and biologically active compounds. This electrochemical process proceeds via the coupling of a benzylic radical and a 1,4-dicyanoarene radical anion to form the desired C-C bond followed by elimination of cyanide anion which woud be trapped as a cyanhydrin by an aldehyde. These radical species are produced by respectively oxidation of the benzylic substrate at the anode and reduction of the dicyanoarene at the cathode. One of the key challenge that we overcame is to avoid the formation of overoxidized coupling products at the bisbenzylic position of the biarylmethane products obtained.


benzylic arylation
C-H functionalization


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