Regio- and stereoselective synthesis of (Z)-β-silylalkenylboranes by silaboration of alkynes catalyzed by palladium and platinum complexes

Article abstract of DOI:10.1016/S0040-4020(99)00444-5

Addition of the silicon-boron bonds of (dimethylphenylsilyl)boranes having pinacol, catechol, and diethylamino groups on the boron across carbon- carbon triple bonds is effectively catalyzed by palladium complexes. The silaboration of a variety of terminal alkynes took place with almost complete regio- and stereoselectivity to afford (Z)-1-boryl-2-silylalkenes in high yields. The silaboration products were subjected to the palladium-catalyzed cross-coupling reaction with aryl iodide and rhodium-catalyzed conjugate addition to methyl vinyl ketone, giving β-silylstyrene derivatives and δ- silyl-γ,δ-unsaturated ketones, respectively, in high yields.