An unprecedented approach for the generation of N-centered radical via a photocatalytic energy transfer process from readily available heterocyclic precursors is reported, which is distinctive to the previous electron transfer approaches. In combination with singlet oxygen, the in situ generated nitrogen radical from oxadiazoline substrate in the presence of fac-Ir(ppy)3 undergoes a selective ipso-addition to arenes to furnish remotely double functionalized spiro-azalactam products.