Iridium-Catalyzed ortho-Selective C–H Silylation of Aromatic Compounds Directed toward the Synthesis of π-Conjugated Molecules with Lewis Acid–Base Interaction

We successfully developed an iridium-catalyzed ortho-selective C–H silylation of aromatic compounds. The reaction exhibited a wide substrate scope, and a variety of π-conjugated molecules were synthesized in good to excellent yields, even in gram scale. Several silyl groups could also be introduced into the products. The experimental results indicated that the regioselectivity could be controlled by a Lewis acid–base interaction between the Lewis acidic silicon atoms of fluorinated hydrosilanes and the Lewis basic nitrogen atoms of aromatic compounds.