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

Authors:

• B. Kopping,
• Chryssostomos Chatgilialoglu,
• M. Zehnder,
• B. Giese

Abstract

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 stereochemistry have been discussed in terms of preferred conformations of the intermediate carbon-centered radicals and are thought to be of steric origin. © 1992, American Chemical Society. All rights reserved.