Silylmetallation of Functionalized Terminal Alkenes

Significance

The chemo- and regioselective silyl­metallation of terminal alkenes which is mediated by a system consisting of SiBNOL-Zn-ate and catalytic CuCN is an extremely valuable development. The reaction is applicable to a broad range of functionalized terminal alkenes. The silyl­ation occurs regioselectively with monosubstituted alkenes at the terminal carbon atom. If two C-C double bonds are present in a molecule, silyl­metallation takes place at the double bond with the smallest number of substituents. The alkylmetal intermediates can be trapped with a number of electrophiles, leading to a variety of functionalized reaction products.