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Synfacts 2007(11): 1178-1178  
DOI: 10.1055/s-2007-991269
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Ammonium Bromides/KF Catalyzed Trifluoromethylation of Carbonyls

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
S. Mizuta, N. Shibata*, M. Hibino, S. Nagano, S. Nakamura, T. Toru*
Nagoya Institute of Technology, Japan
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Publication History

Publication Date:
23 October 2007 (online)

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Significance

The authors report a catalytic tri­fluoromethylation protocol of aldehydes, ketones, and imides which uses inexpensive tetrabutyl­ammonium bromide (TBAB) and KF to activate Me3SiCF3. This system tolerates a wide range of aromatic, alkyl, and conjugated aldehydes as well as cyclic and acylic ketones and cyclic imides. ­Additionally, toluene, CH2Cl2, MeCN, and THF could all be used as solvents. Chiral ammonium salts were then screened in this reaction. With 2-naphth­aldehyde as test substrate, cinchona alkaloid 1 was found to give the corresponding alcohol in 40% ee.