State of the art in the development of biomimetic oxidation catalysts

被引:84
作者
Gonsalves, AMDR
Pereira, MM
机构
[1] Departamento de Química, Universidade de Coimbra
关键词
porphyrin; oxidation; synthesis; hydrogen peroxide; hypochlorite; ligand; metalloporphyrin; chiral porphyrins; epoxidation; hydroxylation;
D O I
10.1016/S1381-1169(96)00050-7
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Work during the last decade laid down the basis for biomimetic oxidation catalysis, which has become an established technique. Preliminary work relied on the use of metal complexes of 5,10,15,20-tetrakisphenylporphyrin (TPP), but these proved to be inadequate to perform the catalytic function. Further, derivatives of TPP with suitable and adequately positioned substituents, allowed the preparation of high performance catalysts, in terms of catalytic efficiency and stability, for some selected oxidations under specific reaction conditions and for a diversity of oxygen donors. The first oxidations were achieved using the 'special' oxygen donor iodosylbenzene, but cheaper and generally available oxidants such as sodium hypochlorite or hydrogen peroxide are presently used as the oxidants. Catalysts capable of promoting stereoselective catalysis are reported. Conditions for the efficient use of the catalysts so far reported require particular specificities and the catalytic activity is only shown, in the majority of the reported works, in the presence of selected species to act as axial ligands to the metal ion of the catalyst. Specific porphyrin structures were reported where the addition of a specific axial ligand can be avoided.
引用
收藏
页码:209 / 221
页数:13
相关论文
共 159 条
[61]   ASYMMETRIC HYDROXYLATION BY A CHIRAL IRON PORPHYRIN [J].
GROVES, JT ;
VISKI, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) :8537-8538
[62]  
GROVES JT, 1985, ISRAEL J CHEM, V25, P148
[63]   REACTIVE IRON PORPHYRIN DERIVATIVES RELATED TO THE CATALYTIC CYCLES OF CYTOCHROME-P-450 AND PEROXIDASE - STUDIES OF THE MECHANISM OF OXYGEN ACTIVATION [J].
GROVES, JT ;
WATANABE, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (25) :8443-8452
[64]   ASYMMETRIC HYDROXYLATION, EPOXIDATION, AND SULFOXIDATION CATALYZED BY VAULTED BINAPHTHYL METALLOPORPHYRINS [J].
GROVES, JT ;
VISKI, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3628-3634
[65]   CATALYTIC ASYMMETRIC EPOXIDATIONS WITH CHIRAL IRON PORPHYRINS [J].
GROVES, JT ;
MYERS, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5791-5796
[66]   HYDROXYLATION AND EPOXIDATION CATALYZED BY IRON-PORPHINE COMPLEXES - OXYGEN-TRANSFER FROM IODOSYLBENZENE [J].
GROVES, JT ;
NEMO, TE ;
MYERS, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (04) :1032-1033
[67]   EPOXIDATION REACTIONS CATALYZED BY IRON PORPHYRINS - OXYGEN-TRANSFER FROM IODOSYLBENZENE [J].
GROVES, JT ;
NEMO, TE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5786-5791
[68]   ROLE OF PYRIDINE IN THE CATALYTIC ACTIVATION OF SODIUM-HYPOCHLORITE IN THE PRESENCE OF MANGANESE PORPHYRIN [J].
GUILMET, E ;
MEUNIER, B .
TETRAHEDRON LETTERS, 1982, 23 (24) :2449-2452
[69]   A NEW CATALYTIC ROUTE FOR THE EPOXIDATION OF STYRENE WITH SODIUM-HYPOCHLORITE ACTIVATED BY TRANSITION-METAL COMPLEXES [J].
GUILMET, E ;
MEUNIER, B .
TETRAHEDRON LETTERS, 1980, 21 (46) :4449-4450
[70]   THE ROLE OF THE AXIAL LIGAND IN MESO-TETRAARYLMETALLOPORPHYRIN MODELS OF THE P-450 CYTOCHROMES [J].
GUNTER, MJ ;
TURNER, P .
JOURNAL OF MOLECULAR CATALYSIS, 1991, 66 (01) :121-141