The palladium‐catalyzed, one‐pot arylative cyclization of 3‐(γ,δ‐disubstituted)allylidene‐2‐oxindoles afforded spirodihydronaphthalene‐2‐oxindole frameworks via an oxidative Heck arylation (Fujiwara–Moritani reaction), an allylic palladium migration, and an aryl C? H bond functionalization/arylation cascade of reactions. This is a first example of the palladium‐catalyzed oxidative arylation and an aryl C? H bond functionalization/arylation cascade reaction which involves an electrophilic arylative quenching of a π‐allylpalladium intermediate and a regio‐controlled aryl C? H bond activation assisted by a weak palladium‐arene interaction.
