Over the past several years, the Pd-catalyzed cross-coupling of silicon compounds has rapidly gained acceptance as a suitable alternative to more commonly known methods such as: Stille (Sn), Kumada (Mg), Suzuki (B), and Negishi (Zn) cross-couplings.
In the presence of a fluoride activation source, alkenyldimethylsilanols readily react with both aryl and alkenyl halides to give the coupled adducts in very good yields. Alternatively, the Pd-catalyzed cross-coupling can also be performed under basic activation using TMSOK for in situ generation of a nucleophilic silanolate. The utility of performing the cross-coupling under basic activation lies in the ability to perform the reaction in the presence of fluoride-sensitive silyl protecting groups. Alkynylsilanols are also active coupling partners under similar conditions.