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Iron‐Catalyzed, Iminyl Radical‐Triggered Cascade 1,5‐Hydrogen Atom Transfer/(5+2) or (5+1) Annulation: Oxime as a Five‐Atom Assembling Unit

Wu Liang, Kun Jiang, Fei Du, Jie Yang, Shuai Li, Qin Ouyang, Ying‐Chun Chen, Ye Wei

2020Angewandte Chemie International Edition51 citationsDOI

Abstract

Abstract By integration of iminyl radical‐triggered 1,5‐hydrogen atom transfer and (5+2) or (5+1) annulation processes, a series of structurally novel and interesting azepine and spiro‐tetrahydropyridine derivatives have been successfully prepared in moderate to good yields. This method utilizes FeCl 2 as the catalyst and readily available oximes as five‐atom units, while showcasing broad substrate scope and good functional group compatibility. The annulation products can be easily converted into many valuable compounds. Moreover, DFT calculation studies are performed to provide some insights into the possible reaction mechanisms for the (5+2) and (5+1) annulations.

Topics & Concepts

AnnulationAzepineHydrogen atomCatalysisChemistryOximeRadicalCombinatorial chemistryAtom (system on chip)PhotochemistryStereochemistryMedicinal chemistryOrganic chemistryGroup (periodic table)Computer scienceEmbedded systemRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques