Electrochemical Dual Trifluoromethylation/Cyclization of 2‐Aryl‐<i>N</i>‐Acryloyl Indoles Enabling Assembly of Indole[2,1‐<i>a</i>]isoquinolines
Abstract An electrochemical cascade radical cyclization of 2‐aryl‐ N ‐acryloyl indoles with sodium trifluoromethanesulfinate as a coupling partner has been explored, which afforded the unexpected bis‐trifluoromethylated indole[2,1‐ a ]isoquinolines as products. Experimental results and DFT calculations disclose that this reaction involves trifluoromethylation‐triggered cyclization and the second trifluoromethylation as the key steps. This strategy does not need any transition‐metal catalysts or oxidants with a readily available trifluoromethylating reagent enabling facile synthesis of bis‐trifluoromethylated indole‐fused tricycles.
Authors
- Lóránd Kiss (ORCID: https://orcid.org/0000-0003-2346-9816)
- Jorge Escorihuela (ORCID: https://orcid.org/0000-0001-6756-0991)
- Haibo Mei (ORCID: https://orcid.org/0000-0002-2857-1935)
- Jianlin Han (ORCID: https://orcid.org/0000-0002-3817-0764)
- Jiang Liu (ORCID: https://orcid.org/0000-0002-8007-1903)
- Yucheng Zhang (ORCID: https://orcid.org/0009-0000-9901-6376)
Institutions
- Universitat de València (ES)
- Nanjing Forestry University (CN)
- Institute of Organic Chemistry (HU)
- HUN-REN Research Centre for Natural Sciences (HU)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2024-11-27
- DOI
- https://doi.org/10.1002/adsc.202401225
- Citations
- 9
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- National Natural Science Foundation of China
- Government of Jiangsu Province
- Hungarian Scientific Research Fund
- Nemzeti Kutatási Fejlesztési és Innovációs Hivatal