Rh(III)-catalyzed allylic C–H amidation of substituted alkenes with in situ generated iminoiodinanes is demonstrated. The presented protocol is compatible with differently functionalized unactivated terminal alkenes and internal alkenes. In terminal alkenes, branch selectivity was observed exclusively. Based on the detailed mechanistic investigation, a possible reaction mechanism involving the in situ generated π-allyl as well as metal–nitrene intermediates has been proposed.