Multistep cascade Pd-catalyzed reactions are useful tools in organic synthesis. Recent advances indicated that oxidation of Pd(II) intermediates into transient Pd(IV) complex could give rise to synthetically attractive C-C bond forming processes. Herein we demonstrate a proof of concept for new annulation reactions based on this concept. A stable palladacycle possessing a Pd-bonded sp3-hybridized stereogenic carbon and featuring a bisimine ligand reacted with diverse allylbromides via a multistep cascade process providing good yields of highly substituted 2H-1-benzoxepines and /or 4H-1-benzopyrans through a sequential formation of two C-C bonds, in some cases involving a Csp2-H activation event.