Mannich reaction using acidic ionic liquids as catalysts and solvents

被引：301

作者：

Zhao, GY ^{[1
]}

Jiang, T ^{[1
]}

Gao, HX ^{[1
]}

Han, BX ^{[1
]}

Huang, J ^{[1
]}

Sun, DH ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Beijing 100080, Peoples R China

来源：

GREEN CHEMISTRY | 2004年 / 6卷 / 02期

关键词：

D O I：

10.1039/b309700p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Several Bronsted acidic ionic liquids were synthesized and successfully used as solvents and catalysts of three-component Mannich reactions of aldehdyes, amines, and ketones at 25degreesC. The used Bronsted acidic ionic liquids include 1-butyl-3-methylimidazolium hydrogen sulfate ([Bmim](+)[HSO4](-)), 1-butyl-3-methylimidazolium dihydrogen phosphate ([Bmim](+)[H2PO4](-)), 1-methylimidazolium p-toluenesulfonic acid ([Hmim](+)Tsa(-)) and 1-methylimidazolium trifluoroacetic acid ([Hmim](+)Tfa(-)). Higher yields were obtained in the presence of [Hmim](+)Tfa(-) in comparison with other Bronsted acidic ionic liquids. The [Hmim](+)Tfa(-) was reused four times without considerable loss of activity.

引用

页码：75 / 77

页数：3

共 19 条

[1] Novel bronsted acidic ionic liquids and their use as dual solvent-catalysts [J].

Cole, AC ;

Jensen, JL ;

Ntai, I ;

Tran, KLT ;

Weaver, KJ ;

Forbes, DC ;

Davis, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5962-5963

[2] Reactions of alkyl azides and ketones as mediated by Lewis acids:: Schmidt and Mannich reactions using azide precursors [J].

Desai, P ;

Schildknegt, K ;

Agrios, KA ;

Mossman, C ;

Milligan, GL ;

Aubé, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7226-7232

[3]

Dupont J., 1999, Org Synth, V79, P236

[4] Proline-catalyzed asymmetric α-amination of aldehydes and ketones -: An astonishingly simple access to optically active α-hydrazino carbonyl compounds [J].

Duthaler, RO .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (09) :975-978

[5] Catalysed esterifications in room temperature ionic liquids with acidic counteranion as recyclable reaction media [J].

Fraga-Dubreuil, J ;

Bourahla, K ;

Rahmouni, M ;

Bazureau, JP ;

Hamelin, J .

CATALYSIS COMMUNICATIONS, 2002, 3 (05) :185-190

[6] The catalytic asymmetric Mannich-type reactions in aqueous media [J].

Kobayashi, S ;

Hamada, T ;

Manabe, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) :5640-5641

[7] The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols [J].

List, B ;

Pojarliev, P ;

Biller, WT ;

Martin, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :827-833

[8] The direct catalytic asymmetric three-component Mannich reaction [J].

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9336-9337

[9] Three-component carbon-carbon bond-forming reactions catalyzed by a Bronsted acid-surfactant-combined catalyst in water [J].

Manabe, K ;

Mori, Y ;

Kobayashi, S .

TETRAHEDRON, 2001, 57 (13) :2537-2544

[10] Mannich-type reactions of aldehydes, amines, and ketones in a colloidal dispersion system created by a Bronsted acid-surfactant-combined catalyst in water [J].

Manabe, K ;

Kobayashi, S .

ORGANIC LETTERS, 1999, 1 (12) :1965-1967

← 1 2 →