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Paper

Org. Biomol. Chem., 2009, 7, 4789 - 4797, DOI: 10.1039/b915077c

Substitution effect on the hydrofluorination reaction of unsaturated amines in superacid HF/SbF5

Fei Liu, Agnès Martin-Mingot, Marie-Paule Jouannetaud, Omar Karam and Sébastien Thibaudeau

This paper describes the scope and limitations of the hydrofluorination reaction in superacid HF/SbF5. On the basis of experimental studies of polyfunctional substrates behaviour, the dramatic effect of substitution on the superelectrophilic character of ammonium–carbenium dications was emphasized. This reaction was applied to the synthesis of novel fluorinated key building blocks. Furthermore, the hydrofluorination reaction and the discovered homodimerization/fluorination reaction were applied to the synthesis of highly valued fluorinated diamines.

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