Nucleophilic Trifluoromethylation of Imines under Acidic Conditions | Zendy

Levin Vitalij V. | Zendy; Dilman Alexander D. | Zendy; Belyakov Pavel A. | Zendy; Struchkova Marina I. | Zendy; Tartakovsky Vladimir A. | Zendy

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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)

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