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- Title
Electrooxidation Enables Selective Dehydrogenative [4+2] Annulation between Indole Derivatives.
- Authors
Song, Chunlan; Liu, Kun; Jiang, Xu; Dong, Xin; Weng, Yue; Chiang, Chien‐Wei; Lei, Aiwen
- Abstract
Dearomative annulation of indoles has emerged as a powerful tool for the preparation of polycyclic indoline‐based alkaloids. Compared with well‐established methods towards five‐membered‐ring‐fused indolines, the six‐membered‐ring‐fused indolines are rarely accessed under thermal conditions. Herein, a dearomative [4+2] annulation between different indoles is developed through an electrochemical pathway. This transformation offers a remarkably regio‐ and stereoselective route to highly functionalized pyrimido[5,4‐b]indoles under oxidant‐ and metal‐free conditions. Notably, this electrochemical approach maintains excellent functional‐group tolerance and can be extended as a modification tactic for pharmaceutical research. Preliminary mechanism studies indicate that the electrooxidation annulation proceeds through radical–radical cross‐coupling between an indole radical cation and an N‐centered radical generated in situ.
- Subjects
INDOLE derivatives; ANNULATION; RADICAL cations; INDOLE
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 18, p7260
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202000226