Hydrosilylation of C−C Multiple Bonds Using (Me3Si)3SiH in Water. Comparative Study of the Radical Initiation Step

Abstract

The classical radical-based hydrosilylation reaction of organic compounds bearing C−C multiple bonds is usually carried out in organic solvents and is herein presented in water with both organic solvent-soluble and water-soluble substrates. Different initiation methods to accomplish the radical-induced hydrosilylation reaction of C−C multiple bonds in water with (Me3Si)3SiH are presented. In the thermal decomposition of azo compounds, the system comprising substrate, silane, and azo-initiator (ACCN) mixed in aqueous medium at 100 °C worked well for both hydrophilic and hydrophobic substrates, with the only variation that the amphiphilic thiol HOCH2CH2SH was also needed in the case of the water-soluble compounds.