Copper() reagent-promoted hydroxytrifluoromethylation of enamides: flexible synthesis of substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one

A novel CuBr-catalyzed hydroxytrifluoromethylation reaction was investigated. Substituted 3-benzylidene-2-arylisoindolin-1-ones was reacted with sodium trifluoromethanesulfinate to afford substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one. The reaction proceeded at 25 °C in...

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Bibliographic Details
Published in:RSC advances 2018-07, Vol.8 (46), p.25961-25965
Main Authors: Wang, Qing, Shi, Peng, Zeng, Runsheng
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemical synthesis
Chemistry
Free radicals
Reagents
Substitutes
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Summary:A novel CuBr-catalyzed hydroxytrifluoromethylation reaction was investigated. Substituted 3-benzylidene-2-arylisoindolin-1-ones was reacted with sodium trifluoromethanesulfinate to afford substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one. The reaction proceeded at 25 °C in air atmosphere in the absence of base and ligands. Our results indicate that trifluoromethyl free radical tends to attack a double bond rather than aryl in this reaction. A novel CuBr-catalyzed hydroxytrifluoromethylation reaction was investigated. Substituted 3-benzylidene-2-arylisoindolin-1-ones were reacted with sodium trifluoromethanesulfinate to afford substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one.
ISSN:2046-2069
2046-2069
DOI:10.1039/c8ra04088e