Pd(0)-Catalyzed Intermolecular Methylene C(sp3)–H Silylation by Using N-Heterocyclic Carbene Ligands

The direct functionalization of methylene C(sp3)–H bonds is one of the greatest challenges in transition metal-catalyzed C–H activation. Although Pd(0)-catalyzed intramolecular cyclization reactions of methylene C(sp3)–H bonds have been reported, intermolecular functionalization remains to be discovered. Herein, we report the first example of a Pd(0)-catalyzed intermolecular methylene C(sp3)–H functionalization reaction. By use of a N-heterocyclic carbene ligand, the methylene C(sp3)–H bonds of 1-(benzyloxy)-2-iodobenzenes are activated and disilylated with hexamethyldisilane, affording disilylated products.