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

卷:70

Article

Amiri, Nesrine^1,2  Le Maux, Paul¹  Srour, Hassan¹  Nasri, Habib²  Simonneaux, Gerard¹ 

[1] CNRS, UMR 6226, Inst Sci Chim Rennes, F-35042 Rennes, France

[2] Univ Monastir, Lab Physicochim Mat, Monastir 5019, Tunisia

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

DOI  :  10.1016/j.tet.2014.10.001

来源: Elsevier

【 摘 要 】

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. (C) 2014 Elsevier Ltd. All rights reserved.

【 授权许可】

Free