A regioselective and Z-selective three-component silylalkoxylation of 1,3-diene using various alcohols, disilane, and a catalytic Pd/Cu/1,4-benzoquinone/O2 system is established in this Letter. The reaction generates tetra-substituted allyl silanes containing allyl ether moieties in up to 80% isolated yield and on a 1-10 mmol scale via oxidative coupling. A wide variety of substrates, including benzyl alcohol derivates, aliphatic alcohols, and bioactive compounds such as cholesterol, are suitable for use in the developed reaction system.