Palladium-catalyzed dehydrogenative amination of polyhydrosiloxanes

Abstract

Palladium-catalyzed dehydrogenative coupling of hydropolysiloxanes with amines was investigated. The reactions of α,ω-dihydropoly(dimethylsiloxane) with pyrrolidine, piperidine, di(isopropyl)amine, and di(n-butyl)amine in the presence of a catalytic amount of PdCl2 or Pd/C at 50–70 °C provided the corresponding aminated polysiloxanes as viscous oils in good to high yields. Poly(dimethylsiloxane-co-hydromethylsiloxane) also underwent the Pd-catalyzed dehydrogenation with pyrrolidine to give the amination product. Treatment of glass surface with the resulting α,ω-bis[di(n-butyl)amino]poly(dimethylsiloxane) increased the surface hydrophobicity, indicating the potential applications of the SiN-containing polysiloxanes as hydrophobic surface modifiers.