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Weinreb Amide Directed Versatile C−H Bond Functionalization under (η 5 ‐Pentamethylcyclopentadienyl)cobalt(III) Catalysis
Author(s) -
Kawai Kentaro,
Bunno Youka,
Yoshino Tatsuhiko,
Matsunaga Shigeki
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801750
Subject(s) - chemistry , catalysis , amide , surface modification , cationic polymerization , cobalt , halogenation , salt (chemistry) , medicinal chemistry , acrylate , combinatorial chemistry , organic chemistry , polymer chemistry , polymer , monomer
The (η 5 ‐pentamethylcyclopentadienyl)cobalt(III) (Cp*Co III )‐catalyzed C−H bond functionalization of aromatic, heteroaromatic, and α,β‐unsaturated Weinreb amides was explored. C−H allylation reactions with the use of allyl carbonate and a perfluoroalkene, oxidative alkenylation reactions with the use of ethyl acrylate, iodination reactions with the use of N ‐iodosuccinimide, and amidation reactions with the use of dioxazolones were catalyzed by Cp*Co(CO)I 2 in the presence of a cationic Ag salt and AgOAc to afford various synthetically useful building blocks. Mechanistic studies of the C−H allylation disclosed that the C−H activation step was rate determining and virtually irreversible.