Iridium-Catalyzed Silylation of Aryl C-H Bonds

摘要

A method for the indium-catalyzed silylation of aryl C-H bonds is described. The reaction of HSiMe(OSiMe_3)_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.