Mild oxidation of alcohols with O-iodoxybenzoic acid (IBX) in ionic liquid 1-butyl-3-methyl-imidazolium chloride and water

被引：95

作者：

Liu, Z ^{[1
]}

Chen, ZC ^{[1
]}

Zheng, QG ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 18期

关键词：

D O I：

10.1021/ol0351549

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A mild, efficient, and eco-friendly procedure for the oxidation of alcohols with IBX in ionic liquid [bmim]Cl and water has been developed. Simply stirring of a solution of the alcohol and IBX in [bmim]Cl/water at room temperature followed by extraction with ether or ethyl acetate and removal of the solvent gives excellent yields of the corresponding carbonyl compounds. Recycling and reuse of the oxidant and ionic liquid have also been reported.

引用

页码：3321 / 3323

页数：3

共 29 条

[1] Hypervalent iodine oxidants: Structure and kinetics of the reactive intermediates in the oxidation of alcohols and 1,2-diols by o-iodoxybenzoic acid (IBX) and Dess-Martin periodinane. A comparative H-1-NMR study [J].

DeMunari, S ;

Frigerio, M ;

Santagostino, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9272-9279

[2] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[3] Ionic liquid (molten salt) phase organometallic catalysis [J].

Dupont, J ;

de Souza, RF ;

Suarez, PAZ .

CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691

[4] A MILD OXIDIZING REAGENT FOR ALCOHOLS AND 1,2-DIOLS - O-IODOXYBENZOIC ACID (IBX) IN DMSO [J].

FRIGERIO, M ;

SANTAGOSTINO, M .

TETRAHEDRON LETTERS, 1994, 35 (43) :8019-8022

[5] OXIDATION OF ALCOHOLS WITH O-IODOXYBENZOIC ACID (IBX) IN DMSO - A NEW INSIGHT INTO AN OLD HYPERVALENT IODINE REAGENT [J].

FRIGERIO, M ;

SANTAGOSTINO, M ;

SPUTORE, S ;

PALMISANO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7272-7276

[6] A user-friendly entry to 2-iodoxybenzoic acid (IBX) [J].

Frigerio, M ;

Santagostino, M ;

Sputore, S .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4537-4538

[7]

Hartmann C., 1893, CHEM BER, V26, P1727

[8] Room temperature ionic liquids as novel media for 'clean' liquid-liquid extraction [J].

Huddleston, JG ;

Willauer, HD ;

Swatloski, RP ;

Visser, AE ;

Rogers, RD .

CHEMICAL COMMUNICATIONS, 1998, (16) :1765-1766

[9] A simple and advantageous protocol for the oxidation of alcohols with, o-iodoxybenzoic acid (IBX) [J].

More, JD ;

Finney, NS .

ORGANIC LETTERS, 2002, 4 (17) :3001-3003

[10]

Mülbaier M, 2001, ANGEW CHEM INT EDIT, V40, P4393, DOI 10.1002/1521-3773(20011203)40:23<4393::AID-ANIE4393>3.0.CO

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