Visible-Light-Induced Cascade Radical Trifluoromethylation/Cyclization/Dearomatization of Isocyanide-Containing Indoles: Synthesis of Trifluoromethylated 3‑Spiroindolines

A visible-light-induced cascade radical trifluoromethylation/cyclization/dearomatization reaction between isocyanide-containing indoles and CF3Br has been developed to afford trifluoromethylated spiro­[indole-3,3-quinoline] and spiro [indole-3,3-pyrrole] derivatives in good yields. The utility of th...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-12, Vol.89 (24), p.18452-18463
Main Authors: Lv, Yuyu, Deng, Zhoubin, Zhu, Zhijun, Wang, Junjiao, Wang, Ke-Hu, Huang, Danfeng, Hu, Yulai
Format: Article
Language:English
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Summary:A visible-light-induced cascade radical trifluoromethylation/cyclization/dearomatization reaction between isocyanide-containing indoles and CF3Br has been developed to afford trifluoromethylated spiro­[indole-3,3-quinoline] and spiro [indole-3,3-pyrrole] derivatives in good yields. The utility of the process is demonstrated by a scale-up experiment. The mechanism was proposed based on the control experiments. The protocol constitutes a novel and efficient route for the synthesis of trifluoromethylated 3-spiroindolenines with advantages of good generality and practical applicability, broad substrate scope, and green energy source.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c02349