Iron-Catalyzed [3 + 2] Annulation of <i>O</i>-Acyl Oximes with 2-Hydroxy-1-Naphthoates for the Synthesis of Benzo[g]indoles
An iron-catalyzed [3 + 2] annulation of <i>O</i>-acyl oximes with 2-hydroxy-1-naphthoates has been developed. This strategy features the simultaneous activation of both substrates to form two radical intermediates. Subsequent selective C-N radical coupling followed by sequential condensation and 1,3-ester migration affords 1<i>H</i>- or 3<i>H</i>-benzo[g]indoles. In terms of the <i>O</i>-acyl oximes derived from 4-oxocyclohexanone and 4-azacyclohexanone, further ring-opening furnishes 2-(2-hydroxyethyl)- or 2-(2-aminoethyl)-1<i>H</i>-benzo[g]indoles.
Authors
- Cang-Hai Yu
- Hai‐Tao Yang (ORCID: https://orcid.org/0000-0001-9803-5452)
- Chun‐Bao Miao (ORCID: https://orcid.org/0000-0003-4666-2619)
- Zhen Cui (ORCID: https://orcid.org/0000-0002-6639-153X)
- Hui Li (ORCID: https://orcid.org/0000-0001-7195-6227)
- Wenya Xu (ORCID: https://orcid.org/0009-0002-9306-2739)
- Wan-Bo Jin
- Xian-Heng Ding
- Xinyu Lyu
- En-Jun Qiao
Institutions
- Ningbo University of Technology (CN)
- Catalytic Materials (United States) (US)
- Jiangsu University of Technology (CN)
- Zhejiang Pharmaceutical College (CN)
- Changzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-05-28
- DOI
- https://doi.org/10.1021/acs.orglett.5c00893
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology Department
- Graduate Research and Innovation Projects of Jiangsu Province