Nitration of Halterman porphyrin: a new route for fine tuning chiral iron and manganese porphyrins with application in epoxidation and hydroxylation reactions using hydrogen peroxide as oxidant

Nesrine Amiri (1, 2) , Paul Le Maux (1) , Hassan Srour (1) , Habib Nasri (2) , Gérard Simonneaux (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 FSM - Faculté des Sciences de Monastir

A methodology is reported for the regioselective nitration of the phenyl groups of Halterman porphyrin, using NaNO2. These nitro-porphyrins can be reduced to aminoporphyrins and then N-dimethylated to give new optically active porphyrins. Applications to the asymmetric epoxidation of styrene derivatives by H2O2 to give optically active epoxides (ee up to 60%) and hydroxylation of alkanes to give optically active secondary alcohols (ee up to 69%) were carried out in organic solvents (dichloromethane/methanol) using chiral iron and manganese porphyrins as catalysts.

Keywords: Tetra-nitro-Halterman porphyrin; Asymmetric epoxidation; Asymmetric hydroxylation; Hydrogen peroxide; Chiral porphyrins

Domains: Chemical Sciences

Nesrine Amiri, Paul Le Maux, Hassan Srour, Habib Nasri, Gérard Simonneaux. Nitration of Halterman porphyrin: a new route for fine tuning chiral iron and manganese porphyrins with application in epoxidation and hydroxylation reactions using hydrogen peroxide as oxidant. Tetrahedron, 2014, 70 (46), pp.8836-8842. ⟨10.1016/j.tet.2014.10.001⟩. ⟨hal-01116078⟩