Details

Autor(en) / Beteiligte

• Lee, Jeonghyo
• Kang, Bora
• Kim, Dongwook
• Lee, Jia
• Chang, Sukbok

Titel

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

Ist Teil von

• Journal of the American Chemical Society, 2021-11, Vol.143 (44), p.18406-18412

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2021

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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.