Copper-Catalyzed Trifluoromethylation of Aryl Iodides with Potassium (Trifluoromethyl)trimethoxyborate

Potassium (trifluoromethyl)trimethoxyborate is introduced as a new source of CF3 nucleophiles in copper‐catalyzed trifluoromethylation reactions. The crystalline salt is stable on storage, easy to handle, and can be obtained in near‐quantitative yields simply by mixing B(OMe)3, CF3SiMe3, and KF. The...

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Bibliographic Details
Published in:Chemistry : a European journal 2011-02, Vol.17 (9), p.2689-2697
Main Authors: Knauber, Thomas, Arikan, Fatih, Röschenthaler, Gerd-Volker, Gooßen, Lukas J.
Format: Article
Language:English
Subjects:
Aromatic compounds
aryl iodide
boron
Catalysis
Chemistry
Conversion
copper
Crystal structure
Handles
Iodides
Nucleophiles
Potassium
synthetic methods
trifluoromethylation
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Summary:Potassium (trifluoromethyl)trimethoxyborate is introduced as a new source of CF3 nucleophiles in copper‐catalyzed trifluoromethylation reactions. The crystalline salt is stable on storage, easy to handle, and can be obtained in near‐quantitative yields simply by mixing B(OMe)3, CF3SiMe3, and KF. The trifluoromethylation reagent allows the conversion of various aryl iodides into the corresponding benzotrifluorides in high yields under mild, base‐free conditions in the presence of catalytic quantities of a CuI/1,10‐phenanthroline complex. Stable reagent: Potassium (trifluoromethyl)trimethoxyborate is introduced as a new source of CF3 nucleophiles in Cu‐catalyzed trifluoromethylation reactions. The stable crystalline salt allows the conversion of aryl iodides into the corresponding benzotrifluorides in high yields under mild, base‐free conditions in the presence of catalytic quantities of a CuI/1,10‐phenanthroline complex (see scheme; FG=functional group).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201002749