Catalytic oxidation of benzene by mononuclear copper(II) complexes with a bis(imidazolyl)methane ligand

被引：0

作者：

Goto, Mana ^{[1
]}

Kajita, Yuji ^{[1
]}

Masuda, Hideki ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY | 2011年 / 50卷 / 3-4期

关键词：

Bioinorganic chemistry; Metalloenzymes; Catalysts; Oxidation; Benzene oxidation; Mononuclear copper; Copper; Bis(benzimidazolyl)methane; D-BETA-M; METAL; OXYGENATION; PHENOL; REACTIVITY; DIOXYGEN; ADDUCT; HYDROXYLATION; METHANE; MODEL;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic oxidation of benzene under mild conditions is one of the most challenging reactions in synthetic chemistry. In order to develop a hydroxylation catalyst for benzene, we have designed and synthesized new copper(II) complexes with the bidentate ligand bis(1,4,5-trimethyl-2-imidazolyl)methane (Me(6)bim), [Cu(Me(6)bim)X-2] (X = Cl, Br). This ligand provides a reaction space which can be easily accessed by exogenous substrates and has an imidazole group, which is a typical ligand of metalloenzymes. These complexes exhibit catalytic oxidation of benzene in the presence of excess H2O2 at room temperature in aqueous MeCN solution to yield phenol and 1,4-benzoquinone.

引用

页码：459 / 464

页数：6

共 39 条

[1] Direct phenol synthesis by selective oxidation of benzene with molecular oxygen on an interstitial-N/Re cluster/zeolite catalyst [J].

Bal, R ;

Tada, M ;

Sasaki, T ;

Iwasawa, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (03) :448-452

[2] Oxidation of methane by a biological dicopper centre [J].

Balasubramanian, Ramakrishnan ;

Smith, Stephen M. ;

Rawat, Swati ;

Yatsunyk, Liliya A. ;

Stemmler, Timothy L. ;

Rosenzweig, Amy C. .

NATURE, 2010, 465 (7294) :115-U131

[3] Direct oxidation of benzene to phenol with hydrogen peroxide over a modified titanium silicalite [J].

Balducci, L ;

Bianchi, D ;

Bortolo, R ;

D'Aloisio, R ;

Ricci, M ;

Tassinari, R ;

Ungarelli, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (40) :4937-4940

[4] The phenol ortho-oxygenation by mononuclear copper( I) complexes requires a dinuclear μ-η2 : η2-peroxodicopper(II) complex rather than mononuclear CuO2 species [J].

Battaini, G ;

De Carolis, M ;

Monzani, E ;

Tuczek, F ;

Casella, L .

CHEMICAL COMMUNICATIONS, 2003, (06) :726-727

[5] METAL-COMPLEXES OF 3 SPARTEINE DIASTEREOISOMERS - PROPERTIES AND REACTIVITIES OF COPPER(II) DERIVATIVES [J].

BOSCHMANN, E ;

WEINSTOCK, LM ;

CARMACK, M .

INORGANIC CHEMISTRY, 1974, 13 (06) :1297-1300

[6]

Burgi H.-B., 1994, STRUCTURE CORRELATIO, V2

[7] Structural and spectroscopic characterization of copper(II) complexes of a new bisamide functionalized imidazole tripod and evidence for the formation of a mononuclear end-on Cu-OOH species [J].

Cheruzel, LE ;

Cecil, MR ;

Edison, SE ;

Mashuta, MS ;

Baldwin, MJ ;

Buchanan, RM .

INORGANIC CHEMISTRY, 2006, 45 (08) :3191-3202

[8]

Creagh D.C., 1992, INT TABLES CRYSTALLO, VC, P219

[9]

Creagh D.C., 1992, INT TABLES CRYST, P200

[10] EXCITED-STATES OF MIXED-LIGAND CHELATES OF RUTHENIUM(II) AND RHODIUM(III) [J].

CROSBY, GA ;

ELFRING, WH .

JOURNAL OF PHYSICAL CHEMISTRY, 1976, 80 (20) :2206-2211

← 1 2 3 4 →