Cobalt-Nitrenoid Insertion-Mediated Amidative Carbon Rearrangement via Alkyl-Walking on Arenes
- Authors
- Lee, Jeonghyo; Kang, Bora; Kim, Dongwook; Lee, Jia; Chang, Sukbok
- Issue Date
- Nov-2021
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.143, no.44, pp.18406 - 18412
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Volume
- 143
- Number
- 44
- Start Page
- 18406
- End Page
- 18412
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/189281
- DOI
- 10.1021/jacs.1c01524
- ISSN
- 0002-7863
- 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.
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