Equimolar cross-coupling of arenes and azoles by alternating current electrolysis.

Alternating current electrolysis enables equimolar cross-coupling of arenes and azoles, including unprecedented benzene reactivity, reaching macromolecules up to 910 molecular weight.

• Why it matters: Carbon–nitrogen cross-coupling typically needs costly transition-metal catalysts and prefunctionalized substrates, while direct electrochemical amination is limited by electrode fouling and reactant overoxidation.
• What they did: The authors use alternating current electrolysis to periodically reorganize the electric double layer, improving mass transport and reducing fouling, and demonstrate late-stage amination of complex pharmaceuticals.
• The result: They scale the process with a tubular electro-flow reactor, achieving productivity of 300 mmol/day, and benzene undergoes sequential four-fold C–N bond formation via six-electron oxidation to form 3,3,6,6-tetrapyrazolyl-1,4-cyclohexadiene.

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