Electrochemical Indole Skeletal Editing via Single-Carbon Atom Insertion
Abstract
Skeletal editing has emerged as a powerful and innovative tool in organic chemistry, offering an efficient approach to the synthesis of complex molecules. Conventional indole skeletal editing approaches predominantly rely on complex carbene precursors and/or transition-metal catalysis to achieve ring expansion. Herein, we report an electrochemical single-carbon insertion strategy for the skeletal editing of indoles into quinolines, which proceeds without the need for specialized reagents or transition-metal catalysts. The reaction is proposed to proceed via an electrooxidative denitrogenation process, in which in situ formed hydrazones generate reactive carbene intermediates that promote ring expansion. This strategy establishes a new activation platform for skeletal editing chemistry.
Fields of Study & Subjects
Radical Photochemical Reactions
Click Chemistry and Applications
Cyclopropane Reaction Mechanisms
Publication details
- Journal / source
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Volume
- 148
- Issue
- 3
- Pages
- 3672–3680
- Publication date
- 12 January 2026
- Language
- EN