Iron-Catalyzed Asymmetric Aerobic Oxidation: Oxidative Coupling of 2-Naphthols

被引：234

作者：

Egami, Hiromichi ^{[1
]}

Katsuki, Tsutomu ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch, Fac Sci, Dept Chem,Higashi Ku, Fukuoka 8128581, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 17期

关键词：

HYDROGEN-PEROXIDE; SULFIDE OXIDATION; CIS-DIHYDROXYLATION; COMPLEXES; EPOXIDATION; DERIVATIVES; NAPHTHOLS; ALKENES;

D O I：

10.1021/ja901391u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fe(salan) complexes were found to be efficient catalysts for the asymmetric aerobic oxidative coupling of 2-naphthol. derivatives. This reaction can be carried out in air at 60 degrees C with high enantioselectivity up to 97% ee. This is the first report for asymmetric aerobic oxidation using molecular oxygen in air in the absence of additives.

引用

页码：6082 / +

页数：3

共 49 条

[1] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[2]

ARMENGOL E, 1999, EUR J ORG CHEM, V191, P5

[3]

Backvall J.-E., 2010, MODERN OXIDATION MET

[4] The current status and future trends in oxidation chemistry [J].

Beller, M .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) :107-108

[5] An efficient oxidative coupling of naphthols catalyzed by Fe impregnated pillared montmorillonite K10 [J].

Bhor, Malhari D. ;

Nandurkar, Nitin S. ;

Bhanushali, Mayur J. ;

Bhanage, Bhalchandra M. .

CATALYSIS LETTERS, 2006, 112 (1-2) :45-50

[6] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[7] Iron-catalyzed oxidation of thioethers by iodosylarenes: Setereoselectivity and reaction mechanism [J].

Bryliakov, Konstantin P. ;

Talsi, Evgenii P. .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (28) :8045-8050

[8] Evidence for the formation of an iodosylbenzene(salen)iron active intermediate in a (salen)iron (III)-catalyzed asymmetric sulfide oxidation [J].

Bryliakov, KP ;

Talsi, EP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5228-5230

[9]

Cheng QF, 2005, CHINESE CHEM LETT, V16, P1467

[10] Chiral oxovanadium complex catalyzed enantioselective oxidative coupling of 2-naphthols [J].

Chu, CY ;

Hwang, DR ;

Wang, SK ;

Uang, BJ .

CHEMICAL COMMUNICATIONS, 2001, (11) :980-981

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