Versatile hypervalent-iodine(III)-catalyzed oxidations with m-chloroperbenzoic acid as a cooxidant

被引：315

作者：

Dohi, T ^{[1
]}

Maruyama, A ^{[1
]}

Yoshimura, M ^{[1
]}

Morimoto, K ^{[1
]}

Tohma, H ^{[1
]}

Kita, Y ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 38期

关键词：

homogeneous catalysis; hypervalent compounds; iodine; oxidation; synthetic methods;

D O I：

10.1002/anie.200501688

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A new and effective use of hypervalent iodine(III) reagents as catalysts involves the transformation of iodoarenes 1 into hypervalent iodine(III) species 2 with meta-chloroperbenzoic acid (mCPBA) as the appropriate cooxidant. With observed turnover numbers greater than 70, this procedure paves the way for broader application of these useful oxidants in organic synthesis. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6193 / 6196

页数：4

共 25 条

[1] OXIDATION OF ALKYL AND ARYL IODIDES, PHENYLACETALDEHYDE AND ALKENES BY DIMETHYLDIOXIRANE - REACTION-PRODUCTS AND MECHANISM [J].

BRAVO, A ;

FONTANA, F ;

FRONZA, G ;

MINISCI, F ;

SERRI, A .

TETRAHEDRON LETTERS, 1995, 36 (38) :6945-6948

[2] A unique site-selective reaction of ketones with new recyclable hypervalent iodine(III) reagents based on a tetraphenylmethane structure [J].

Dohi, T ;

Maruyama, A ;

Yoshimura, M ;

Morimoto, K ;

Tohma, H ;

Shiro, M ;

Kita, Y .

CHEMICAL COMMUNICATIONS, 2005, (17) :2205-2207

[3] ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .14. ELECTROCHEMISTRY OF HYPERVALENT COMPOUNDS .2. THE FIRST ELECTROSYNTHESIS OF HYPERVALENT IODOBENZENE DIFLUORIDE DERIVATIVES AND ITS APPLICATION TO INDIRECT ANODIC GEM-DIFLUORINATION [J].

FUCHIGAMI, T ;

FUJITA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) :7190-7192

[4] Electrochemical fluorination of β-dicarbonyl compounds using p-iodotoluene difluoride as a mediator [J].

Hara, S ;

Hatakeyama, T ;

Chen, SQ ;

Ishi-i, K ;

Yoshida, M ;

Sawaguchi, M ;

Fukuhara, T ;

Yoneda, N .

JOURNAL OF FLUORINE CHEMISTRY, 1998, 87 (02) :189-192

[5]

Kazmierczak P, 1998, SYNTHESIS-STUTTGART, P1721

[6] Syntheses of (diacetoxyiodo)arenes or iodylarenes from iodoarenes, with sodium periodate as the oxidant [J].

Kazmierczak, P ;

Skulski, L ;

Kraszkiewicz, L .

MOLECULES, 2001, 6 (11) :881-891

[7] Hypervalent iodine reagents in organic synthesis: Nucleophilic substitution of p-substituted phenol ethers [J].

Kita, Y ;

Takada, T ;

Tohma, T .

PURE AND APPLIED CHEMISTRY, 1996, 68 (03) :627-630

[8] HYPERVALENT IODINE OXIDATION OF N-ACYLTYRAMINES - SYNTHESIS OF QUINOL ETHERS, SPIROHEXADIENONES, AND HEXAHYDROINDOL-6-ONES [J].

KITA, Y ;

TOHMA, H ;

KIKUCHI, K ;

INAGAKI, M ;

YAKURA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :435-438

[9] Recent progress in the use of hypervalent iodine reagents in organic synthesis. A review [J].

Kitamura, T ;

Fujiwara, Y .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1997, 29 (04) :409-458

[10] FURTHER FUNCTIONAL-GROUP OXIDATIONS USING SODIUM PERBORATE [J].

MCKILLOP, A ;

KEMP, D .

TETRAHEDRON, 1989, 45 (11) :3299-3306

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