A cobalt−N-heterocyclic carbene catalyst promotes a tandem radical cyclization/C−C coupling reaction between tosylamide-tethered bromo-alkenes and aryl N−H imines initiated by chelation-assisted arene C−H activation, affording 3-(arylmethyl)pyrrolidine derivatives in moderate to good yields. The reaction tolerates a variety of substituents on the aryl imine as well as various modifications on the bromo- alkene substrate.