Zirconocene-mediated coupling of bis(methoxyethynyl)disilanes (1a and 1e-g) led to zirconacycles (2a and 2e-g), which were converted into 3,4-dialkylidene- and 3,4-benzo-1,2-disilacyclobutanes (3a and 6e-g) via protonolysis and transmetallation with tin followed by Diels-Alder reaction. Their Si-Si bonds were reactive toward palladium catalyst to give bissilylation and silyl-Heck products (8, 9 and 10).