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Electrophilic indoles bearing a leaving group at C2 undergo C3-regioselective dearomative hydroaryloxylation and subsequent 1,2-tertiary alkyl migration/aromatization. This is the first ring-opening migration of the spiroindolenine intermediate formed by the C3 nucleophilic addition reaction. Various spiro-oxindole-chromeno[3,2-b]/[2,3-b]indoles were successfully synthesized in excellent yields (up to 98%). This reaction features selective ring-opening migration (C−C/C−O) of the tertiary alkyl group from the indole C3 position to the C2 position stereoselectively, providing a unique synthetic method for constructing novel polycyclic indole skeletons.