Organosilicon compounds have been extensively utilized both in industry and academia. Studies on the syntheses of diverse organosilanes is highly appealing. Through‐space metal/hydrogen shifts allow functionalization of C−H bonds at a remote site, which are otherwise difficult to achieve. However, until now, an aryl to alkyl 1,5‐palladium migration process seems to have not been presented. Reported herein is the remote olefination, arylation, and borylation of a methyl group on silicon to access diverse vinyl‐, benzyl‐, and borylsilanes, constituting a unique C(sp3)−H transformation based on a 1,5‐palladium migration process. Shifting positions: Reported here is the remote olefination, arylation, and borylation of a methyl group on silicon, constituting a unique C(sp3)−H transformation based on a 1,5‐palladium migration process. It provides a powerful and efficient synthetic method starting from simple unfunctionalized organosilanes and leading to diverse vinyl‐, benzyl‐, and borylsilanes.