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Jeonghyo, Lee
분자활성 촉매반응 연구단
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Cobalt-Nitrenoid Insertion-Mediated Amidative Carbon Rearrangement via Alkyl-Walking on Arenes

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Title
Cobalt-Nitrenoid Insertion-Mediated Amidative Carbon Rearrangement via Alkyl-Walking on Arenes
Author(s)
Jeonghyo Lee; Bora Kang; Dongwook Kim; Jia Lee; Sukbok Chang
Publication Date
2021-11-10
Journal
Journal of the American Chemical Society, v.143, no.44, pp.18406 - 18412
Publisher
American Chemical Society
Abstract
© 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.
URI
https://pr.ibs.re.kr/handle/8788114/10852
DOI
10.1021/jacs.1c10138
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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