Ruthenium-catalyzed C-H silylation of methylboronic acid was achieved by use of 2-(1H-pyrazol-3-yl)aniline as a removable alpha-directing modifier on the boron atom. Cross-coupling of the product, i.e., (phenyldimethylsilyl)methylpinacolborane, with aryl halides proceeded in the presence of a [PdCl2(dppf)] catalyst and CsOH as a base.