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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

Abstract : 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.
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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, Elsevier, 2014, 70 (46), pp.8836-8842. ⟨10.1016/j.tet.2014.10.001⟩. ⟨hal-01116078⟩

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