A palladium-catalyzed three-component tandem reaction for stereoselective assembly of various tri- or tetrasubstituted vinylsilanes is established. This method enables the construction of two C–Si bonds and two C–C bonds by the disilylation of ortho-vinyl bromobenzenes generated in situ from 1-bromo-2-iodobenzenes and N-tosylhydrazones. More importantly, the substrate scope of this protocol was further demonstrated by the transformation of ortho-vinyl bromobenzenes generated from a range of aryl iodides and N-tosylhydrazone to vinylsilanes.