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

Abstract

The direct functionalization of methylene C(sp 3 )−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(sp 3 )−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(sp 3 )−H functionalization reaction. By use of a Nheterocyclic carbene ligand, the methylene C(sp 3 )−H bonds of 1-(benzyloxy)-2-iodobenzenes are activated and disilylated with hexamethyldisilane, affording disilylated products.