H2O2/NaHCO3-mediated enantioselective epoxidation of olefins in NTf2-based ionic liquids and under ultrasound

Gregory Chatel (1, 2) , Catherine Goux-Henry (2) , Anaïs Mirabaud (1) , Thomas Rossi (1) , N. Kardos (1) , Bruno Andrioletti (2) , M. Draye (1)

1 LCME - Laboratoire de Chimie Moléculaire et Environnement
2 CASYEN - Catalyse Synthèse et Environnement

The bicarbonate-activated peroxide (BAP) system has been shown to constitute an excellent and versatile combination for the epoxidation of olefins. Herein, we demonstrate that the benign H2O2/NaHCO3 oxidative combination can be used for the enantioselective epoxidation of olefins using a chiral manganese porphyrin as a catalyst. This unprecedented result was made possible by the use of an ionic liquid with ultrasound, which leads to the activation of Mn-porphyrin catalysis.

Mots clés: Enantioselective catalysis; Ultrasound; Ionic liquids; Mn-porphyrin; Epoxidation

Domaines: Chimie organique; Chimie; Catalyse

Gregory Chatel, Catherine Goux-Henry, Anaïs Mirabaud, Thomas Rossi, N. Kardos, et al.. H2O2/NaHCO3-mediated enantioselective epoxidation of olefins in NTf2-based ionic liquids and under ultrasound. Journal of Catalysis, 2012, 291, pp.127-132. ⟨10.1016/j.jcat.2012.04.016⟩. ⟨hal-01160231⟩