New manganese β-polynitroporphyrins as particularly efficient catalysts for biomimetic hydroxylation of aromatic compounds with H2O2

被引：52

作者：

Bartoli, JF ^{[1
]}

Mouries-Mansuy, V ^{[1
]}

Le Barch-Ozette, K ^{[1
]}

Palacio, M ^{[1
]}

Battioni, P ^{[1
]}

Mansuy, D ^{[1
]}

机构：

[1] Univ Paris 05, UMR 8601, F-75270 Paris 06, France

来源：

CHEMICAL COMMUNICATIONS | 2000年 / 10期

关键词：

D O I：

10.1039/b001776k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of Mn porphyrins bearing one to eight beta-nitro substituents were synthesized in high yield in three steps by using a new general method for selective nitration of a Zn(meso-tetraarylporphyrin); this Mn porphyrin series exhibits a remarkably wide span of Mn(III)/Mn(II) redox potentials from -290 to + 1150 mV (vs. SCE), and the Mn porphyrins bearing one to five beta-nitro groups are particularly good catalysts for hydroxylation of aromatic compounds with H2O2, with yields up to 98, 83, 80 and 12%, respectively for anisole, naphthalene, acetanilide and ethylbenzene.

引用

页码：827 / 828

页数：2

共 15 条

[1] BIOMIMETIC HYDROXYLATION OF AROMATIC-COMPOUNDS - HYDROGEN-PEROXIDE AND MANGANESE-POLYHALOGENATED PORPHYRINS AS A PARTICULARLY GOOD SYSTEM
CARRIER, MN
SCHEER, C
GOUVINE, P
BARTOLI, JF
BATTIONI, P
MANSUY, D
[J]. TETRAHEDRON LETTERS, 1990, 31 (46) : 6645 - 6648
[2] NIH SHIFT IN HAEMIN-IODOSYLBENZENE-MEDIATED HYDROXYLATIONS
CHANG, CK
EBINA, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (15) : 778 - 779
[3] DOLPHIN D, 1998, ACCOUNTS CHEM RES, V31, P155
[4] Groves John T., 1995, P3
[5] HOFFMANN P, 1992, B SOC CHIM FR, V129, P85
[6] IKIDA K, 1994, CHEM LETT, P1307
[7] Lindsay-Smith J.R., 1982, J CHEM SOC P2, V2, P1009
[8] ACTIVATION OF ALKANES - THE BIOMIMETIC APPROACH
MANSUY, D
[J]. COORDINATION CHEMISTRY REVIEWS, 1993, 125 (1-2) : 129 - 141
[9] METALLOPORPHYRINS AS VERSATILE CATALYSTS FOR OXIDATION REACTIONS AND OXIDATIVE DNA CLEAVAGE
MEUNIER, B
[J]. CHEMICAL REVIEWS, 1992, 92 (06) : 1411 - 1456
[10] Meunier B., 2000, PORPHYRIN HDB, V4, P119

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