title: Iridium-catalyzed silylation of aryl C-H bonds.
abstract: 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.
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Chen
authors.initials: C
authors.lastname: Cheng
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig