The palladium-catalyzed direct cross-coupling of a range of organic chlorides and bromides with the bifunctional C(sp(3))-(trimethylsilyl)methyllithium reagent is reported. The use of Pd-PEPPSI-IPent as the catalyst allows for the preparation of structurally diverse and synthetically versatile benzyl- and allylsilanes in high yields under mild conditions (room temperature) with short reaction times.