Visible-Light-Induced\nCascade Radical Trifluoromethylation/Cyclization/Dearomatization\nof Isocyanide-Containing Indoles: Synthesis of Trifluoromethylated\n3‑Spiroindolines

A visible-light-induced cascade radical trifluoromethylation/cyclization/dearomatization\nreaction between isocyanide-containing indoles and CF<sub>3</sub>Br\nhas been developed to afford trifluoromethylated spiro[indole-3,3-quinoline]\nand spiro [indole-3,3-pyrrole] derivatives in good yields. The utility\nof the process is demonstrated by a scale-up experiment. The mechanism\nwas proposed based on the control experiments. The protocol constitutes\na novel and efficient route for the synthesis of trifluoromethylated\n3-spiroindolenines with advantages of good generality and practical\napplicability, broad substrate scope, and green energy source.

Publication Details

Journal
Figshare
Published
2024-12-04
DOI
https://doi.org/10.1021/acs.joc.4c02349.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Visible-Light-Induced\nCascade Radical Trifluoromethylation/Cyclization/Dearomatization\nof Isocyanide-Containing Indoles: Synthesis of Trifluoromethylated\n3‑Spiroindolines

Figshare
Fluorine in Organic Chemistry
article

Visible-Light-Induced\nCascade Radical Trifluoromethylation/Cyclization/Dearomatization\nof Isocyanide-Containing Indoles: Synthesis of Trifluoromethylated\n3‑Spiroindolines

article en

Abstract

A visible-light-induced cascade radical trifluoromethylation/cyclization/dearomatization\nreaction between isocyanide-containing indoles and CF<sub>3</sub>Br\nhas been developed to afford trifluoromethylated spiro[indole-3,3-quinoline]\nand spiro [indole-3,3-pyrrole] derivatives in good yields. The utility\nof the process is demonstrated by a scale-up experiment. The mechanism\nwas proposed based on the control experiments. The protocol constitutes\na novel and efficient route for the synthesis of trifluoromethylated\n3-spiroindolenines with advantages of good generality and practical\napplicability, broad substrate scope, and green energy source.

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Fluorine in Organic Chemistry
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