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Nucleophilic Trifluoromethylation of Imines under Acidic Conditions
Author(s) -
Levin Vitalij V.,
Dilman Alexander D.,
Belyakov Pavel A.,
Struchkova Marina I.,
Tartakovsky Vladimir A.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800820
Subject(s) - trifluoromethylation , chemistry , chemoselectivity , iminium , nucleophile , electrophile , hydrofluoric acid , group (periodic table) , organic chemistry , combinatorial chemistry , medicinal chemistry , ion , trifluoromethyl , catalysis , alkyl
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)