Authors
Feng-Shuo Bao, Jichao Huang, Zhihan Zhang, Xiao-Ye Yu, Cui-Yang Fang, Dong-Qi Dai, Jing Huang, Min Jiang, Anastasios Polyzos, Wen-Jing Xiao, Jia-Rong Chen
Published in
Angewandte Chemie (International ed. in English). Pages e5282902. Oct 19, 2026. Epub Oct 19, 2026.
Abstract
Dearomative hydrofunctionalization of indoles represents an appealing strategy to access C(sp3)-rich indoline scaffolds for drug discovery; however, such transformations typically require activated substrates, leaving unactivated indoles largely unexplored. Herein, we report a photochemical radical carbonylative dearomatization of unactivated indoles under visible light irradiation. Central to this protocol is the interception of the highly reactive indolenium intermediate-generated in situ via acid-mediated C3-protonation-through the formation of an electron donor-acceptor (EDA) complex with 4-alkyl-1,4-dihydropyridines (DHPs). This photoactive EDA complex initiates a mechanistically distinct radical pathway that effectively circumvents the detrimental dimerization typically plaguing indolenium intermediates. Subsequent radical carbonylation and radical cross-coupling enable the carbonylative dearomatization of a broad range of indoles with diverse alkyl-DHPs. The method exhibits excellent functional group tolerance and broad substrate scope, furnishing various 2-acylindolines in generally good yields. Comprehensive mechanistic studies, including control experiments, electron paramagnetic resonance spectroscopy, and UV/vis absorption analyses, support a radical-radical coupling mechanism as the key step in this transformation.
PMID:
42895372
Bibliographic data and abstract were imported from PubMed on 19 Oct 2026.
Read full publication at:
Please sign in
to see all details.
Advertisement
Stats
- Recommendations n/a n/a positive of 0 vote(s)
- Views 13
- Comments 0