Palladium-catalyzed dimerization disilylation of 1,3-butadiene with chlorosilanes.
[reaction: see text] 1,3-Butadiene reacted with chlorosilanes and Grignard reagents at 20 degrees C in the presence of a catalytic amount of Pd(acac)(2) to give disilylated dimers 2 regioselectively, which have two silyl groups (R(3)Si) at the 3- and 8-positions of a 1,6-octadiene skeleton. When phenyl- or allyl-substituted chlorosilanes were used, coupling product was obtained stereo- as well as regioselectively, giving rise to only (E)-olefins. It is proposed that Pd-ate complexes play important roles in both C-Si bond-forming processes.
Terao
Jun
J
Department of Molecular Chemistry & Science and Technology Center for Atoms, Molecules and Ions Control, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Oda
Akihiro
A
Kambe
Nobuaki
N