Electrochemical Dual Trifluoromethylation/Cyclization of 2-Aryl- N-Acryloyl Indoles Enabling Assembly of Indole[2,1-a]isoquinolines

Mei, Haibo and ZHANG, Yucheng and JIANG, LIU and Jorge, Escorihuela and Kiss, Loránd and Han, Jianlin (2025) Electrochemical Dual Trifluoromethylation/Cyclization of 2-Aryl- N-Acryloyl Indoles Enabling Assembly of Indole[2,1-a]isoquinolines. ADVANCED SYNTHESIS & CATALYSIS, 367 (3). No.-e202401225. ISSN 1615-4150

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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.

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