An efficient and general copper(I)-catalyzed method for the synthesis of multi-substituted vinylsilanes is reported. Multi-substituted allenes with electron-withdrawing groups and propiolate derivatives reacted well with (dimethylphenylsilyl)boronic acid pinacol ester to afford silyl-substituted butenoate derivatives and β-silyl-substituted acrylate derivatives, respectively. The corresponding products could be obtained in moderate to high yields and with good to excellent stereoselectivities.