Acidic-functionalized ionic liquid as an efficient, green and reusable catalyst for hetero-Michael addition of nitrogen, sulfur and oxygen nucleophiles to α,β-unsaturated ketones

被引：46

作者：

Han, Feng ^{[1
,2
,3
]}

Yang, Lei ^{[1
,2
]}

Li, Zhen ^{[1
,2
]}

Xi, Chungu ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Lanzhou 730000, Peoples R China

[3] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 02期

关键词：

BETA-AMINO ACIDS; CONJUGATE ADDITION; STEREOSELECTIVE-SYNTHESIS; SOLVENTS; ENONES; ESTERS; BASE;

D O I：

10.1039/c1ob06346d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of acidic-functionalized ionic liquids were synthesized and applied to the hetero-Michael addition of nitrogen, sulfur and oxygen nucleophiles to alpha,beta-unsaturated ketones under solvent-free conditions. Notably, 1-methylimidazolium p-toluenesulfonic ([Hmim]OTs) was found to be the most efficient catalyst and could realize "homogeneous catalysis, two-phase separation". Additionally, the catalytic system has wide substrate scope and good to excellent yields (up to 99%) could be obtained at room temperature.

引用

页码：346 / 354

页数：9

共 48 条

[1] Chemistry of pyrazino[2,1-b]quinazoline-3,6-diones [J].

Avendaño, C ;

Menéndez, JC .

CURRENT ORGANIC CHEMISTRY, 2003, 7 (02) :149-173

[2] Tetrahydropyran Synthesis by Intramolecular Conjugate Addition to Enones: Synthesis of the Clavosolide Tetrahydropyran Ring [J].

Bates, Roderick W. ;

Song, Ping .

SYNTHESIS-STUTTGART, 2010, (17) :2935-2942

[3] Synthesis of novel β-functionalized α-oximinoketones via hetero-Michael addition of alcohols and mercaptans to enones [J].

Bernal, P ;

Tamariz, J .

TETRAHEDRON LETTERS, 2006, 47 (17) :2905-2909

[4] Addition of hydrogen sulfide to methyl acrylate over solid basic catalysts [J].

Breysse, E ;

Fajula, F ;

Finiels, A ;

Frémy, G ;

Tichit, D ;

Moreau, C .

JOURNAL OF CATALYSIS, 2005, 233 (02) :288-296

[5] Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids [J].

Cardillo, G ;

Tomasini, C .

CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :117-&

[6] Michael additions catalyzed by transition metals and lanthanide species.: A review [J].

Comelles, J ;

Moreno-Mañas, M ;

Vallribera, A .

ARKIVOC, 2005, :207-238

[7] Stereoselective synthesis of 2-aryloxy esters: An asymmetric approach to fluoxetine, tomoxetine and nisoxetine [J].

Devine, PN ;

Heid, RM ;

Tschaen, DM .

TETRAHEDRON, 1997, 53 (20) :6739-6746

[8] Ionic Liquids Made with Dimethyl Carbonate: Solvents as well as Boosted Basic Catalysts for the Michael Reaction [J].

Fabris, Massimo ;

Lucchini, Vittorio ;

Noe, Marco ;

Perosa, Alvise ;

Selva, Maurizio .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (45) :12273-12282

[9] Derailing the Wacker oxidation: Development of a palladium-catalyzed amidation reaction [J].

Gaunt, MJ ;

Spencer, JB .

ORGANIC LETTERS, 2001, 3 (01) :25-28

[10] Ionic Liquids with a Twist: New Routes to Liquid Salts [J].

Giernoth, Ralf .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (33) :5608-5609

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