Dearomatization of Electron-Deficient Indoles with <i>N</i>-Alkylanilines via Visible-Light-Induced Hydroalkylation
Herein, a visible-light-induced, base-promoted 3 + 2 annulation was developed for the dearomatization of electron-deficient indoles with readily available <i>N</i>-alkylanilines, affording valuable tetrahydropyrrolo[3,4-<i>b</i>]indol-1(2<i>H</i>)-ones with high diastereoselectivity. This protocol features excellent atom economy, a broad substrate scope with exceptional functional group tolerability, and compatibility with continuous-flow conditions. Mechanistic studies suggest that photoredox catalysis generates <i>N</i>-α-carbon radicals, which undergo radical addition to indoles, followed by amidation, providing an efficient and scalable route to indoline derivatives.
Authors
- Wengang Xu (ORCID: https://orcid.org/0000-0002-8468-8468)
- Fengyu Ma
- Yifan Liu (ORCID: https://orcid.org/0000-0002-1785-4614)
- Qihang Xu (ORCID: https://orcid.org/0000-0003-4515-1526)
- Mingbo Wu (ORCID: https://orcid.org/0000-0003-0048-778X)
- Qiao Zhang (ORCID: https://orcid.org/0000-0001-9682-3295)
- Hong Shan (ORCID: https://orcid.org/0000-0002-8896-5813)
Institutions
- Qingdao University of Science and Technology (CN)
- China University of Petroleum, East China (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-11
- DOI
- https://doi.org/10.1021/acs.orglett.5c01933
- Citations
- 5
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 4.68
Funders
- Department of Science and Technology of Shandong Province
- National Natural Science Foundation of China
- China Postdoctoral Science Foundation
- Natural Science Foundation of Shandong Province