N‑Trifluoromethylation of Nitrosoarenes with Sodium Triflinate

A highly efficient N-trifluoromethylation of nitrosoarenes is reported. The inexpensive and convenient Langlois reagent (sodium triflinate) is employed as a CF3-radical source in combination with a copper catalyst and an oxidant. N-Trifluoromethylated hydroxylamines are obtained in high yields withi...

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Veröffentlicht in:Organic letters 2017-05, Vol.19 (9), p.2374-2377
Hauptverfasser: van der Werf, Angela, Hribersek, Matic, Selander, Nicklas
Format: Artikel
Sprache:eng
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Zusammenfassung:A highly efficient N-trifluoromethylation of nitrosoarenes is reported. The inexpensive and convenient Langlois reagent (sodium triflinate) is employed as a CF3-radical source in combination with a copper catalyst and an oxidant. N-Trifluoromethylated hydroxylamines are obtained in high yields within 1 h at room temperature. The addition of hydroquinone was found to be instrumental to prevent the formation of side products. The method is high-yielding, is scalable, and displays a high functional group tolerance.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.7b00908