We have developed a Cp*Co(III)-catalyzed reverse regioselective [4 + 2] annulation of N-chlorobenzamides/acrylamides with vinylsilanes for the synthesis of 4-silylated isoquinolones. The reaction was performed at ambient temperature under redox-neutral conditions. The reaction utilized the N-Cl bond as an internal oxidant, furnished the required products with excellent regioselectivities, and demonstrated high functional group tolerance. The synthetic utility of 4-silylated isoquinolones has been demonstrated for the preparation of 4-heteroarylated and 4-alkylated isoquinolones via metal-free C-C couplings. Additionally, 3,4-dihydroisoquinolones were synthesized via protodesilylation of 4-silylated isoquinolones, thus making vinylsilane an ethylene surrogate.