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Cobalt–Nitrenoid Insertion-Mediated Amidative Carbon Rearrangement via Alkyl-Walking on Arenes by Jeonghyo Lee; Bora Kang; Dongwook Kim; Jia Lee; Sukbok Chang is a Chemistry article available to read on EtoBox.

What is Cobalt–Nitrenoid Insertion-Mediated Amidative Carbon Rearrangement via Alkyl-Walking on Arenes about?

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 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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Author

Jeonghyo Lee; Bora Kang; Dongwook Kim; Jia Lee; Sukbok Chang

Publisher

American Chemical Society (ACS)

Published

2021

Language

EN

Field

Chemistry (Physical Sciences)