Ionic and covalent copper(II)-based catalysts for Michael additions.: The mechanism

被引：41

作者：

Comelles, J

Moreno-Mañas, M

Pérez, E

Roglans, A

Sebastián, RM

Vallribera, A

机构：

[1] Univ Autonoma Barcelona, Dept Chem, E-08193 Barcelona, Spain

[2] Univ Girona, Dept Chem, Girona 17071, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 20期

关键词：

D O I：

10.1021/jo049373z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cu(SbF6)(2)-AdamBox and copper(II) bis-(5-tert-butylsalicylaldehydate) catalyze the Michael addition in neutral media. Mechanistic studies, based on UV-vis, IR, and electrospray ionization mass spectrometry (ESI-MS), suggest that copper enolates of the beta-dicarbonyl formed in situ are the active nucleophilic species.

引用

收藏

页码：6834 / 6842

页数：9

相关论文

共 89 条

[11] Characterization of reactive intermediates in palladium-catalyzed arylation of methyl acrylate (Heck reaction) [J].

Brown, JM ;

Hii, KK .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (06) :657-659

[12] Enantioselective catalysis - Part 124. Enantioselective Michael reaction catalyzed by optically active transition metal complexes [J].

Brunner, H ;

Krumey, C .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 142 (01) :7-15

[13] Electrospray ionization tandem mass spectrometry in high-throughput screening of homogeneous catalysts [J].

Chen, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (25) :2832-2847

[14] SOLVENT-DERIVED METAL-OXIDES IN ELECTROSPRAY MASS-SPECTROMETRY OF METAL SALT-SOLUTIONS [J].

CHENG, ZL ;

SIU, KWM ;

GUEVREMONT, R ;

BERMAN, SS .

ORGANIC MASS SPECTROMETRY, 1992, 27 (12) :1370-1376

[15]

CHISTOFFERS J, 2000, EUR J ORG CHEM, P701

[16]

CHISTOFFERS J, 1999, TETRAHEDRON, V55, P5377

[17]

Christoffers J, 2000, ANGEW CHEM INT EDIT, V39, P2752, DOI 10.1002/1521-3773(20000804)39:15<2752::AID-ANIE2752>3.0.CO

[18]

2-5

[19] Formation of quaternary stereocenters by copper-catalyzed Michael reactions with L-valine amides as auxiliaries [J].

Christoffers, J .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (20) :4862-4867

[20] Regioselective enamine formation from oxonia-boranuida-betaines and their application in asymmetric Michael reactions [J].

Christoffers, J ;

Kreidler, B ;

Unger, S ;

Frey, W .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (15) :2845-2853

← 1 2 3 4 5 6 7 8 9 →