Access to Tetrahydropyrido[1,2-<i>a</i>]indol-6-one Derivatives via NHC-Catalyzed Radical Dearomatization of Indoles
Tetrahydropyrido[1,2-<i>a</i>]indol-6-one is a significant motif that is widely present in natural bioactive alkaloids. Herein, a facile and efficient access to the tetrahydropyrido[1,2-<i>a</i>]indol-6-one skeleton via NHC (N-heterocyclic carbene)-catalyzed radical relay dearomatization of indoles has been developed. This protocol exhibits metal-free, mild reaction conditions, a broad substrate scope, high efficiency, and excellent diastereoselectivity (30 examples, up to 89% yield and >20:1 dr).
Authors
- Tianjiao Huang (ORCID: https://orcid.org/0009-0003-3775-1940)
- Tuanjie Li (ORCID: https://orcid.org/0000-0002-0886-5485)
- Changsheng Yao (ORCID: https://orcid.org/0000-0002-0185-2366)
- Kai Zhang (ORCID: https://orcid.org/0000-0001-9341-0444)
- Chenxia Yu
Institutions
- Jiangsu Normal University (CN)
- State Key Laboratory of Synthetic Chemistry (CN)
- Green Chemistry (PL)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-04
- DOI
- https://doi.org/10.1021/acs.orglett.5c02563
- Citations
- 1
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Jiangsu Province
- Natural Science Research of Jiangsu Higher Education Institutions of China