Nucleophilic Trifluoromethylation of Imines under Acidic Conditions

✍ Scribed by Vitalij V. Levin; Alexander D. Dilman; Pavel A. Belyakov; Marina I. Struchkova; Vladimir A. Tartakovsky

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 156 KB
• Volume: 2008
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200800820

✦ Synopsis

Abstract

A general method for the trifluoromethylation of imines by using Me~3~SiCF~3~ under acidic conditions is described. The reaction is promoted by hydrofluoric acid generated in situ from KHF~2~ and either TFA or TfOH. A new chemoselectivity pattern was achieved, as the C=N bond was found to be more reactivate than the carbonyl group. The trifluoromethylation reaction is believed to proceed by concerted transfer of the CF~3~ group from the silicon atom to the iminium electrophile. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)