Dications in superacid HF/SbF5: When superelectrophilic activation makes possible fluorination and/or C-H bond activation

A. Martin-Mingot (1) , G. Compain (1) , Franklin Liu (1) , M.P. Jouannetaud (1) , C. Bachmann (2) , G. Frapper (2) , S. Thibaudeau (1)

1 SRSN - Synthèse et réactivité des substances naturelles
2 LACCO - Laboratoire de catalyse en chimie organique

The reactivity of aliphatic amides/ketones/imines and nitriles was studied in superacid HF/SbF5 in the presence of CCI4. After the identification of the reaction intermediates by in situ NMR experiments, we propose that the sp(3)C-H bond functionalization (fluorination) by the superacid system is strongly dependant on the superelectrophilic character of the distonic dicationic intermediates.

Domaines: Catalyse; Chimie organique; Autre

A. Martin-Mingot, G. Compain, Franklin Liu, M.P. Jouannetaud, C. Bachmann, et al.. Dications in superacid HF/SbF5: When superelectrophilic activation makes possible fluorination and/or C-H bond activation. Journal of Fluorine Chemistry, 2012, 134 (SI), pp.56-62. ⟨10.1016/j.jfluchem.2011.04.022⟩. ⟨hal-00826922⟩