Abstract Cp*Co III ‐catalyzed highly regioselective mono‐ and bis‐annulation of arylamides with 1,3‐diynes using N −OMe as an internal oxidant is demonstrated. This atom‐economical transformation does not require any external oxidant and tolerates many functional groups. Various symmetrical and unsymmetrical heterocycles (homo and hetero) are accessed with predictable regio‐ and chemoselectivity.