Electroreductive generation of nitrosoarenes: application towards the nitroso Diels–Alder reaction

Herein, we report a simplified protocol for the electroreduction of nitroarenes, avoiding the use of stoichiometric reducing metals or sacrificial electrodes. Alternating current electrolysis enabled fine control over the selective generation of elusive nitrosoarenes, reducing dramatically the formation of side overreduction products. The developed conditions were also compatible with the nitroso Diels-Alder reaction of various cyclic dienes, allowing easy access to azabicyclo[2.2.2]octene derivatives.