10.1021/acscatal.7b00928.s002 Hongwei Zhang Hongwei Zhang Kilian Muñiz Kilian Muñiz Selective Piperidine Synthesis Exploiting Iodine-Catalyzed C<sub>sp</sub><sup>3</sup>–H Amination under Visible Light American Chemical Society 2017 light initiation free-radical-promoted piperidine formation iodine catalyst terminal oxidant halogen coordination 30 applications pyrrolidine synthesis sp Visible Light nitrogen intermediates piperidine formation hydrocarbon amination reaction 2017-05-10 00:00:00 Dataset https://acs.figshare.com/articles/dataset/Selective_Piperidine_Synthesis_Exploiting_Iodine-Catalyzed_C_sub_sp_sub_sup_3_sup_H_Amination_under_Visible_Light/5011979 A route to selective piperidine formation through intramolecular catalytic C<sub>sp</sub><sup>3</sup>–H amination is described. This hydrocarbon amination reaction employs a homogeneous iodine catalyst derived from halogen coordination between molecular iodine and a terminal oxidant. It relies on visible light initiation and proceeds within two catalytic cycles that comprise a radical C–H functionalization and an iodine-catalyzed C–N bond formation. Under these conditions, the commonly observed preference for pyrrolidine synthesis based on halogenated nitrogen intermediates within the Hofmann–Löffler domain is effectively altered in favor of a free-radical-promoted piperidine formation. The protocol is demonstrated for a total of 30 applications.