Abstract The competition between CH activation and Heck reactions has been studied on 2‐alkenyl‐substituted o‐iodobenzylpyrroles. The reaction can be switched from the alkene to the pyrrole nucleus by choosing the adequate catalytic system, regardless of the nature of the substituent on the alkene, obtaining excellent yields of pyrrolo[1,2‐b]isoquinolines or pyrrolo[2,1‐a]isoindoles.