We have recently reported highly efficient conditions for the palladium-catalyzed silylation of terminal alkenes using trimethylsilyl halides, which give rise to allyl or vinyl silanes depending on the nature of the starting material. In an effort to expand and improve the scope of this chemistry, we have now identified a second-generation catalyst that promotes the formation of allyl silanes with significantly improved yields (up 95%). We have also identified conditions that allow for the direct preparation of vinyl siloxy ethers from terminal alkenes, which are highly efficient substrates Denmark-Hiyama cross-coupling reactions. The development of these new processes, as well as the scope and limitations of both will be discussed.

Improved reaction conditions for the silyl-Heck reaction

244th National Meeting (2012)

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