Substitution effect on the hydrofluorination reaction of unsaturated amines in superacid HF/SbF(5).
This paper describes the scope and limitations of the hydrofluorination reaction in superacid HF/SbF(5). 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.
Laboratoire Synthèse et Réactivité des Substances Naturelles, UMR 6514, 40, avenue du Recteur Pineau, F-86022, Poitiers Cedex, France.
Fei
F
Liu
Agnès
A
Martin-Mingot
Marie-Paule
MP
Jouannetaud
Omar
O
Karam
Sébastien
S
Thibaudeau
D000588:Amines / Q000737:chemistry*; D000965:Antimony / Q000737:chemistry*; D002412:Cations / Q000737:chemistry; D019281:Dimerization; D005459:Fluorides / Q000737:chemistry*; D054879:Halogenation; D006858:Hydrofluoric Acid / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry
D000588:Amines; D002412:Cations; C529140:antimony pentafluoride; D000965:Antimony; D009584:Nitrogen; D005459:Fluorides; D006858:Hydrofluoric Acid