Iridium-Catalyzed Silylation of Aryl C−H Bonds

A method for the iridium-catalyzed silylation of aryl C–H bonds is described. The reaction of HSiMe(OSiMe₃)₂ with arenes and heteroarenes catalyzed by the combination of [Ir(cod)(OMe)]₂ and 2,4,7-trimethylphenanthroline occurs with the aromatic compound as the limiting reagent and with high levels of sterically derived regioselectivity. This new catalytic system occurs with a much higher tolerance for functional groups than the previously reported rhodium-catalyzed silylation of aryl C–H bonds and occurs with a wide range of heteroarenes. The silylarene products are suitable for further transformations, such as oxidation, halogenation, and cross-coupling. Late-stage functionalization of complex pharmaceutical compounds was demonstrated. Read more on publisher's site.