%0 Journal Article %A Zhang, Hongwei %A Muñiz, Kilian %D 2017 %T Selective Piperidine Synthesis Exploiting Iodine-Catalyzed Csp3–H Amination under Visible Light %U https://acs.figshare.com/articles/journal_contribution/Selective_Piperidine_Synthesis_Exploiting_Iodine-Catalyzed_C_sub_sp_sub_sup_3_sup_H_Amination_under_Visible_Light/5011982 %R 10.1021/acscatal.7b00928.s001 %2 https://acs.figshare.com/ndownloader/files/8447093 %K light initiation %K free-radical-promoted piperidine formation %K iodine catalyst %K terminal oxidant %K halogen coordination %K 30 applications %K pyrrolidine synthesis %K sp %K Visible Light %K nitrogen intermediates %K piperidine formation %K hydrocarbon amination reaction %X A route to selective piperidine formation through intramolecular catalytic Csp3–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. %I ACS Publications