Tris(trimethylsilyl)silane: an efficient hydrosilylating agent of alkenes and alkynes

• DOI: 10.1021/jo00040a048
• Publication Date: 2005-03-18T00:36:01Z
• Authors: B. Kopping; C. Chatgilialoglu; M. Zehnder; B. Giese
• Keywords: 01 natural sciences; 0104 chemical sciences

tris(trimethylsilyl)silane adds across the double bond of a variety of mono-, di-, and trisubstituted under free-radical conditions in good yields. The reaction, which proceeds via a free-radical chain mechanim, 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 term of preferred conformations of the intermediate carbon-centered radicals and are thought to be of steric origin