Angewandte Chemie. International edition in English 2012-06-25

Direct electrophilic N-trifluoromethylation of azoles by a hypervalent iodine reagent.

Katrin Niedermann, Natalja Früh, Remo Senn, Barbara Czarniecki, René Verel, Antonio Togni

Index: Angew. Chem. Int. Ed. Engl. 26th ed., 51 , 6511-6515, (2012)

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Abstract

Effective CF(3) transfer: Various electron-rich nitrogen heterocycles (pyrazoles, triazoles, and tetrazoles) can be directly N-trifluoromethylated by a hypervalent iodine reagent in an efficient manner. The optimized procedure, which includes an in situ silylation of the substrate followed by an acid-catalyzed CF(3) transfer, provides ready access to a series of new and previously challenging or inaccessible NCF(3) compounds.Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.