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

被引：32

作者：

Amiri, Nesrine ^{[1
,2
]}

Le Maux, Paul ^{[1
]}

Srour, Hassan ^{[1
]}

Nasri, Habib ^{[2
]}

Simonneaux, Gerard ^{[1
]}

机构：

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

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

来源：

TETRAHEDRON | 2014年 / 70卷 / 46期

关键词：

Tetra-nitro-Halterman porphyrin; Asymmetric epoxidation; Asymmetric hydroxylation; Hydrogen peroxide; Chiral porphyrins; CATALYZED ASYMMETRIC EPOXIDATIONS; ENANTIOSELECTIVE EPOXIDATION; AROMATIC ALKENES; NONHEME IRON; H2O2; OXIDATION; OLEFINS; METAL; COMPLEXES; FE;

D O I：

10.1016/j.tet.2014.10.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：8836 / 8842

页数：7

共 48 条

[1] Metal-catalyzed asymmetric epoxidations of terminal olefins using hydrogen peroxide as the oxidant [J].

Arends, Isabel W. C. E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (38) :6250-6252

[2] MONOOXYGENASE-LIKE OXIDATION OF HYDROCARBONS BY H2O2 CATALYZED BY MANGANESE PORPHYRINS AND IMIDAZOLE - SELECTION OF THE BEST CATALYTIC-SYSTEM AND NATURE OF THE ACTIVE OXYGEN SPECIES [J].

BATTIONI, P ;

RENAUD, JP ;

BARTOLI, JF ;

REINAARTILES, M ;

FORT, M ;

MANSUY, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (25) :8462-8470

[3] Electronically tuned chiral ruthenium porphyrins: Extremely stable and selective catalysts for asymmetric epoxidation and cyclopropanation [J].

Berkessel, A ;

Kaiser, P ;

Lex, J .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (19) :4746-4756

[4] SYNTHESIS OF GYROSCOPE-LIKE PORPHYRINS [J].

BOITREL, B ;

LECAS, A ;

RENKO, Z ;

ROSE, E .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (24) :1820-1821

[5] Active sites and mechanisms of bioinspired oxidation with H2O2, catalyzed by non-heme Fe and related Mn complexes [J].

Bryliakov, Konstantin P. ;

Talsi, Evgenii P. .

COORDINATION CHEMISTRY REVIEWS, 2014, 276 :73-96

[6] REGIOSELECTIVE AND ENANTIOSELECTIVE EPOXIDATION CATALYZED BY METALLOPORPHYRINS [J].

COLLMAN, JP ;

ZHANG, XM ;

LEE, VJ ;

UFFELMAN, ES ;

BRAUMAN, JI .

SCIENCE, 1993, 261 (5127) :1404-1411

[7] PICKET-FENCE PORPHYRINS - SYNTHETIC MODELS FOR OXYGEN BINDING HEMOPROTEINS [J].

COLLMAN, JP ;

GAGNE, RR ;

REED, CA ;

HALBERT, TR ;

LANG, G ;

ROBINSON, WT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1427-1439

[8] Recent advances in catalytic asymmetric epoxidation using the environmentally benign oxidant hydrogen peroxide and its derivatives [J].

De Faveri, Giorgio ;

Ilyashenko, Gennadiy ;

Watkinson, Michael .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (03) :1722-1760

[9] Asymmetric heterogeneous carbene transfer catalyzed by optically active ruthenium spirobifluorenylporphyrin polymers [J].

Ferrand, Y ;

Poriel, C ;

Le Maux, P ;

Rault-Berthelot, J ;

Simonneaux, G .

TETRAHEDRON-ASYMMETRY, 2005, 16 (08) :1463-1472

[10] Catalytic asymmetric oxidation of sulfide and styrene derivatives using macroporous resins containing chiral metalloporphyrins (Fe, Ru) [J].

Ferrand, Yann ;

Daviaud, Romain ;

Le Maux, Paul ;

Simonneaux, Grard .

TETRAHEDRON-ASYMMETRY, 2006, 17 (06) :952-960

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