Hetero-Diels-Alder Reaction of Alkenes and Electrochemically- Generated o-Quinonediimines

Electrochemically driven organic transformations have emerged as a versatile approach for developing more sustainable synthetic methods, offering precise control over redox processes while replacing stoichiometric oxidants with electricity. In this context, an efficient electrochemical strategy for the generation of highly reactive o-quinonediimines from readily available o-phenylenediamines is reported. Anodic oxidation enables their in-situ formation and subsequent cycloaddition with diverse alkenes, affording valuable tetrahydroquinoxaline cycloadducts in good to excellent yields. The broad substrate scope, together with the successful derivatization of the products, highlights the synthetic utility of this approach.