Addition of Silicon−Silicon σ-Bonds to Arynes or Bisarynes Catalyzed by a Palladium Complex

Addition reactions of the silicon−silicon σ-bonds of disilanes to the carbon−carbon triple bonds of various arynes are promoted by a palladium-1,1,3,3-tetramethylbutyl isocyanide complex to give diverse 1,2-disilylated arenes. Five-membered and benzo-condensed six-membered cyclic disilanes were applicable to the bissilylation, whereas reactions using four- or seven-membered cyclic disilanes or acyclic disilanes did not produce the desired insertion products at all. Bisarynes, containing two strained triple bonds in a molecule, could also insert into the silicon−silicon bond smoothly to afford tetrasilylated arenes in modest yields.