Iron polypyridyl complex-catalyzed oxidative radical cyclization with nucleophilic α-amino radicals and electron-deficient olefins was achieved. Iron polypyridyl complexes have a range of redox potential (E_1/2 = +0.82~1.10 V), which could oxidize tertiary amines, anilines and enamines (E_ox = 0.8~1.0 V).¹ One electron oxidation of tertiary amine by Fe(III) complex and further deprotonation of amine radical cation offers nucleophilic α-amino radical species, which is reactive to N-substituted maleimides and electron-deficient alkenes.² Under optimal condition, we synthesized various tetrahydroquinoline derivatives. Additionally, the synthetic utility of this reaction was presented in the further transformation to pyrroloquinoline and tetrahydropyridazinedione of products.³ Herein, we present oxidative cycloaddition of tertiary amines with electron-deficient olefins under easy operation and high catalytic efficiency. Acknowledgement This work supported by the GRRC program of Gyeonggi province (GRRCKyungHee2017-A01) and National Research Foundation (NRF-2015R1D1A1A01060349). Reference 1. a) Ju, X.; Li, D.; Li, W.; Yu, W.; Bian, F., Adv. Synth. Catal. 2012, 354, 3561. b) Comito, R. J.; Finelli, F. G.; MacMillan, D. W. C., J. Am. Chem. Soc. 2013, 135, 9358. 2. Zhu, S.; Das, A.; Bui, L.; Zhou, H.; Curran, D. P.; Reuping, M., J. Am. Chem. Soc. 2013, 135, 1823. 3. Nishino, M.; Hirano, K.; Satoh, T.; Miura, M., J. Org. Chem. 2011, 76, 6447.