Nucleophilic Trifluoromethylation of Imines under Acidic Conditions

作者：Levin Vitalij V; Dilman Alexander D^*; Belyakov Pavel A; Struchkova Marina I; Tartakovsky Vladimir A

来源：European Journal of Organic Chemistry, 2008, 2008(31): 5226-5230.

DOI：10.1002/ejoc.200800820

• Fluorine
• Imines
• Schiff bases
• Silicon
• Trifluoromethylation

A general method for the trifluoromethylation of imines by using Me3SiCF3 under acidic conditions is described. The reaction is promoted by hydrofluoric acid generated in situ from KHF2 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 CF3 group from the silicon atom to the iminium electrophile.

• 出版日期2008-11