Simplified Preparation of Trialkylvinylsilanes via the Silyl-Heck Reaction Utilizing a Second Generation Catalyst

Recently we reported a second generation ligand, bis(3,5-di-tert-butylphenyl)(tert-butyl)-phosphine, for the preparation of allylsilanes using the silyl-Heck reaction. We now show that this new ligand also provides superior reactivity in the preparation of vinylsilanes from styrene derivatives. For the first time, this new ligand provides exceptionally high yields of trialkylvinylsilanes using the widely available palladium pre-catalyst, tris(dibenzylidene-acetone) dipalladium(0) [Pd-2(dba)(3)]. Finally, we demonstrate that this new catalyst system is able to form more highly decorated all-carbon substituted vinylsilanes that have been shown to possess superior reactivity in oxidation and cross-coupling reactions.