Silicone as an organosilicon reagent for the palladium-catalyzed cross-coupling reaction

Silicone, poly(diorganosiloxane), serves as an organosilicon reagent for palladium-catalyzed cross-coupling reactions. Treatment of poly[(aryl)methylsiloxane], poly[(alkenyl)methylsiloxane], or cyclic oligosiloxanes with various aryl iodides in the presence of silver(I) oxide (Ag2O) or tetrabutylammonium fluoride (TBAF) and a catalytic amount of palladium affords the corresponding cross-coupling product in a good to excellent yield. The reaction of silicone with aryl chlorides in the presence of K2CO3/H2O as an activator proceeded to afford biaryl derivatives in moderate to excellent yields. A wide range of aryl chlorides bearing an electron-donating or electron-withdrawing substituent on the aromatic ring are tolerated.