An efficient protocol has been developed for the intramolecular oxidative oxyarylation using a PdII-catalyzed tandem oxypalladation/CH functionalization strategy. This methodology allows rapid access to tetrahydro-2H-indeno-[2,1-b]furan frameworks from simple hydroxyalkenes. The reactivity of this process is orthogonal to that of Pd0-catalyzed transformations, enabling the divergent modification of a single molecule.