Homocoupling reaction of unsaturated silanes in aqueous micelles

Palladium-promoted homocoupling reaction of vinyl- and polyenylsilanes in aqueous conditions has been investigated. The reaction is catalyzed by PdCl(2) in the presence of the re-oxidizing system CuCl(2)/LiCl and occurs at room temperature in aqueous solutions containing nonionic amphiphiles. Symmetrically alpha,omega-disubstituted stereodefined all-trans polyenes have been obtained in mild conditions and in good yields (65-87%), higher than those previously reported for the same reactions carried out in methanol or HMPA. A comparison between two commercially available surfactants, Triton X-100 and PTS, has been performed.