Palladium-catalyzed cross-coupling reactions of heterocyclic silanolates with substituted aryl iodides and bromides

Sodium silanolates derived from a number of heterocyclic silanols undergo cross-coupling with a variety of aromatic iodides and bromides under mild conditions. In situ deprotonation of the silanols with an equivalent amount of sodium hydride in toluene generates the sodium salt that couples with iodides under the action of Pd₂(dba)₃·CHCl₃ in good yield at room temperature to 50 °C. The aromatic bromides also couple with these salts under the action of the Pd(I) catalyst 12.