Cobalt-Nitrenoid Insertion-Mediated Amidative Carbon Rearrangement via Alkyl-Walking on Arenes

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We herein disclose the Cp*Co(III)(LX)-catalyzed amidative alkyl migration using 2,6-disubstituted phenyl azidoformates. Upon the cobalt- nitrenoid insertion toward the substituted ortho carbon, an arenium cationic species bearing a quaternary carbon is generated, and a subsequent alkyl migration process is suggested to occur through an unforeseen alkyl-walking mechanism. A quinolinol ligand of the cobalt catalyst system is proposed to facilitate the final product-releasing rearomatization process by serving as an internal base. This new mechanistic mode enabled both [1,2]- and [1,4]-alkyl rearrangements to allow the structural variation of N-heterocyclic compounds.
Publisher
AMER CHEMICAL SOC
Issue Date
2021-11
Language
English
Article Type
Article
Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.143, no.44, pp.18406 - 18412

ISSN
0002-7863
DOI
10.1021/jacs.1c10138
URI
http://hdl.handle.net/10203/289667
Appears in Collection
CH-Journal Papers(저널논문)
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