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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
Author(s) -
Liang Wu,
Jiang Kun,
Du Fei,
Yang Jie,
Shuai Li,
Ouyang Qin,
Chen YingChun,
Wei Ye
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202007825
Subject(s) - annulation , azepine , hydrogen atom , catalysis , chemistry , oxime , radical , combinatorial chemistry , atom (system on chip) , photochemistry , stereochemistry , medicinal chemistry , organic chemistry , group (periodic table) , computer science , embedded system
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.