[Cu]/NFSI-Mediated Cascade Diels-Alder Radical Annulations Using Norbornene as H-Acceptor under Redox-Neutral Conditions.

An oxidative cascade [4 + 2] radical cycloaddition/dehydroaromatization reaction of aryl alkenes to access α-aryl substituted naphthalenes under redox-neutral conditions was achieved. This reaction was found to require the addition of [Cu] catalyst along with stoichiometric concentrations of NFSI as a trigger of radical series of steps. Norbornene (NBE), rather than the conventional oxidant, manifested optimal performances as a H-acceptor in this procedure. The results herein might shed encouraging insight into the transition-metal-catalyzed dehydrogenative C-H activation protocols.