A New Method for Hypersilyl Aromatic Compounds

Significance

Incorporation of the tris(trimethyl­silyl) group, known as hypersilyl group, into π-conjugated compounds is a promising strategy for the development of unique optoelectronic materials. This super-sterically demanding functionality can not only suppress π-π stacking, which often leads to emission quenching, but also offers effective σ-π conjugation with adjacent π-electron systems. Nevertheless, synthetic methods for hypersilylated compounds have been quite limited, which often accompany cleavage of weak Si-Si σ-bonds. Herein, the authors communicate the palladium-catalyzed cross-coupling of tris(trimethyl)silane with aryl iodides to provide hypersilylated aromatic compounds, leaving the Si-Si bonds intact. Furthermore, they show that other hydrooligosilanes are applicable to this reaction.