Transition Metal-catalyzed Silylation of Organic Halides with Hydrosilanes

Since arylsilanes are versatile reagents for carbon-carbon bond formation, the supply of functionalized and reactive arylsilanes has become more necessary. We demonstrated the first example of the palladium (0) -catalyzed silylation of aryl halides with triethoxysilane as a silicon source and affording the corresponding aryltriethoxysilanes. Although this catalyst system has lacked the wide applicability to functionalized substrates, we found that a rhodium (I) complex overcomes a number of limitations of the palladium (0) -catalyzed silylation. The silylation of aryl iodides with hydrosilanes was able to apply to 1,1,1,3,5,5,5-heptamethyltrisiloxane by the appropriate choice of catalyst systems. 3-Aryl-1,1,1,3,5,5,5-heptamethyltrisiloxanes were also provided by platinum-catalyzed dehydrogenative coupling with aromatic hydrocarbons. These catalytic silylations supply a wide range of functionalized arylsiloxanes.