(Me3Si)3SiH: An Efficient Hydrosilylating Agent of Alkenes and Alkynes

Article abstract of DOI:10.1021/jo00040a048

Tris(trimethylsilyl)silane adds across the double bond of a variety of mono-, di-, and trisubstituted olefins under free-radical conditions in good yields.The reaction, which proceeds via a free-radical chain mechanism, is highly regioselective (anti-Markovnikov).Addition to prochiral olefins bearing an ester group is highly stereoselective.The factors that control the sterochemistry have been discussed in terms of preferred conformations of the intermediate carbon-centered radicals and are thought to be of steric origin.