We report herein an extensive investigation of simple and regioselective endo- as well as exo-γ-arylations of silyl-dienol ethers of unblocked cyclic enones with the utilization of palladium-catalyzed, modified Kuwajima-Urabe conditions. We have also successfully explored a new exo-ε-arylation of silyl-trienol ethers of π-extended cyclic enones. In addition, we also report, herein, exclusive γ- and ε-alkenylation of silyl-dienol and silyl-trienol ethers of cyclic enones.