Palladium and nickel catalysts promoted highly selective carbon–carbon bond insertion reactions with di-tert-butyl-alkylidenesilacyclopropanes. Pd(PPh3)4 was demonstrated to be the optimal catalyst, allowing for a variety of carbon–carbon π-bond insertion reactions. Depending on the nature of the carbon–carbon π bond, the insertion reaction proceeded with either direct insertion into the carbon(sp2)–silicon bond or with allylic transposition. Ring-substituted alkylidenesilacyclopropanes required a nickel catalyst to afford insertion products. Using Ni(cod)2 as the carbon–carbon bond insertion catalyst, new double alkyne insertion products and alkene isomerization products were observed.
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