Bicyclo [4.3. 0] nonanes (hydrindanes) and bicyclo [3.3. 0] octanes (octahydropentalenes) are easily synthesized by palladium-catalyzed cycloalkenylations. Additionally, benzo-fused bicyclo [3.3. 0] octanes are prepared for the first time through intramolecular coupling between silyl enol ethers and aromatic rings in the presence of catalytic palladium acetate.