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Iron‐Catalyzed Aminative Cyclization/Intermolecular Homolytic Aromatic Substitution Using Oxime Esters and Simple Arenes
Author(s) -
Shimbayashi Takuya,
Okamoto Kazuhiro,
Ohe Kouichi
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201701634
Subject(s) - chemistry , homolysis , alkene , regioselectivity , electrophilic aromatic substitution , catalysis , intermolecular force , bond cleavage , alkyl , oxime , alkylation , medicinal chemistry , organic chemistry , molecule , radical
Intermolecular C−H alkylation of simple arenes in the presence of an iron catalyst has been achieved in a cascade manner with an aminative cyclization triggered by N−O bond cleavage of an alkene‐tethered oxime ester. Various arenes, including electron‐rich and electron‐poor arenes, and heteroarenes can be employed in the reaction system. Regioselectivity and radical trapping experiments support the involvement of alkyl radical species, which undergo a homolytic aromatic substitution (HAS) to afford the arylation products.