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

[1] OBSERVATION OF CATALYTIC INTERMEDIATES IN THE SUZUKI REACTION BY ELECTROSPRAY MASS-SPECTROMETRY [J].

ALIPRANTIS, AO ;

CANARY, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6985-6986

[2] Michael reactions promoted by η1-O-enolatoruthenium(II) complexes derived from Ru(cod)(cot), diphosphine, and dimethyl malonate [J].

Alvarez, SG ;

Hasegawa, S ;

Hirano, M ;

Komiya, S .

TETRAHEDRON LETTERS, 1998, 39 (29) :5209-5212

[3]

[Anonymous], 1979, FUNDAM RES HOMOGENEO

[4] Electrospray ionization mass spectrometry detection of intermediates in the palladium-catalyzed oxidative self-coupling of areneboronic acids [J].

Aramendía, MA ;

Lafont, F ;

Moreno-Mañas, M ;

Pleixats, R ;

Roglans, A .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3592-3594

[5]

Bartoli G, 1999, EUR J ORG CHEM, V1999, P617

[6] BiCl3 or CdI2 catalyzed Michael addition of 1,3-dicarbonyl compounds under microwave irradiations [J].

Baruah, B ;

Boruah, A ;

Prajapati, D ;

Sandhu, JS .

TETRAHEDRON LETTERS, 1997, 38 (08) :1449-1450

[7] MICHAEL ADDITION OF BETA-DICARBONYLS TO ALPHA,BETA UNSATURATED-KETONES CATALYZED BY MIXED SPHERE BETA-CARBONYLENOLATE DIPHOSPHINO METAL-COMPLEXES [J].

BASATO, M ;

CORAIN, B ;

DERONI, P ;

FAVERO, G ;

JAFORTE, R .

JOURNAL OF MOLECULAR CATALYSIS, 1987, 42 (01) :115-125

[8] Synthesis and structure of enantiomerically pure platinum complexes of phosphino-oxazolines and their use in asymmetric catalysis [J].

Blacker, AJ ;

Clarke, ML ;

Loft, MS ;

Mahon, MF ;

Williams, JMJ .

ORGANOMETALLICS, 1999, 18 (15) :2867-2873

[9] LANTHANIDES IN ORGANIC-SYNTHESIS - EU+3-CATALYZED MICHAEL ADDITION OF 1,3-DICARBONYL COMPOUNDS [J].

BONADIES, F ;

LATTANZI, A ;

ORELLI, LR ;

PESCI, S ;

SCETTRI, A .

TETRAHEDRON LETTERS, 1993, 34 (47) :7649-7650

[10] ASYMMETRIC MICHAEL ADDITIONS CATALYZED BY NI(II) AND CO(II) COMPLEXES WITH HOMOCHIRAL LIGANDS [J].

BOTTEGHI, C ;

PAGANELLI, S ;

SCHIONATO, A ;

BOGA, C ;

FAVA, A .

JOURNAL OF MOLECULAR CATALYSIS, 1991, 66 (01) :7-21

← 1 2 3 4 5 6 7 8 9 →