A new route to rare porphyrinoids: The non-innocence of the corrole ring allows the oxidative ring insertion of a nitrogen atom under mild conditions (see scheme; NBS=N-bromosuccinimide). The resulting meso-substituted azaporphyrins exhibit high-energy Soret absorption bands and red luminescence. This new synthetic route will allow for the development of novel azaporphyrin complexes with relevance to the study of biomimetic oxidations.