Palladium- and Nickel-Catalyzed Carbon-Carbon Bond Insertion Reactions with Alkylidenesilacyclopropanes.
Palladium and nickel catalysts promoted highly selective carbon-carbon bond insertion reactions with di-tert-butyl-alkylidenesilacyclopropanes. Pd(PPh(3))(4) was demonstrated to be the optimal catalyst, allowing for a variety of carbon-carbon pi-bond insertion reactions. Depending on the nature of the carbon-carbon pi bond, the insertion reaction proceeded with either direct insertion into the carbon(sp(2))-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.
Buchner
Kay M
KM
Department of Chemistry, University of California, Irvine, CA 92697-2025.
Woerpel
K A
KA