N-(Trifluoromethyl)imine derivatives are prepared via acid-catalyzed electrophilic trifluoromethylation of nitriles in the presence of azoles (see scheme) using 1, a readily prepared and easy-to-handle hypervalent iodine(III) reagent. This Ritter-type reaction constitutes a straightforward method for the preparation of N-(trifluoromethyl)imidoyl azoles which are otherwise very difficult to access. Such a reaction is unprecedented and represents a fundamentally new access to NCF3 derivatives by formation of the N-CF3 bond. 

Direct electrophilic trifluoromethylation at nitrogen atoms using hypervalent iodine reagents: A new Ritter-type reaction

242nd National Meeting (2011)

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