We report herein a palladium-catalyzed distal alkylation of silyldienol and silyltrienol ethers of enones through coupling with activated halides to achieve new endo- and exo-alkylated motifs. Additionally, by employing propargyl bromides, synthetically useful linear allenes along with functionalized enones have been synthesized. Low-catalyst loading, and late-stage transformations of pharmaceutically relevant molecules further showcase the importance of the present protocol.