Cu(II) homogeneous and heterogeneous catalysts for the asymmetric Henry reaction

被引：39

作者：

Jones, Matthew D. ^{[1
]}

Cooper, Christine J.

Mahon, Mary F. ^{[1
]}

Raithby, Paul R.

Apperley, David ^{[2
]}

Wolowska, Joanna ^{[3
]}

Collison, David ^{[3
]}

机构：

[1] Univ Bath, Dept Chem, Bath Chem Crystallog Unit, Bath BA2 7AY, Avon, England

[2] Univ Durham, Dept Chem, Solid State NMR Serv, Durham DH1 3LE, England

[3] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2010年 / 325卷 / 1-2期

基金：

英国工程与自然科学研究理事会;

关键词：

Homogeneous and heterogeneous catalysts; Copper; Supported catalysts; BOND-FORMING REACTIONS; COPPER(II) COMPLEXES; NITROALDOL REACTION; CRYSTAL-STRUCTURES; LIGANDS; EFFICIENT; TRANS-1,2-DIAMINOCYCLOHEXANE; BIS(OXAZOLINE); DERIVATIVES; DIAMINE;

D O I：

10.1016/j.molcata.2010.03.013

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

New Cu(II) complexes have been prepared and characterised via single crystal X-ray diffraction studies, EPR spectroscopy, elemental analysis and high resolution mass spectrometry. In all cases 1:2 (copper to ligand) stoichiometric complexes were isolated. The homogeneous Cu(II) complexes were tested for the asymmetric Henry reaction. Conversions in excess of 70% were obtained with enantioselectivities in the range 0-78%. Heterogeneous Cu(II) catalysts have been prepared. In these cases high conversions were obtained. However, after prolonged reaction time the main product observed was 1,3-dinitro-2-phenyl propane. The formation of this product can be curtailed by both decreasing the catalyst loading and employing shorter reaction times. (C) 2010 Elsevier B.V. All rights reserved.

引用

页码：8 / 14

页数：7

共 56 条

[41] Syntheses and X-ray structures of Cu(II) and Zn(II) complexes of N,N′-dibenzyl-(R,R)-1,2-diaminocyclohexane and application to nitroaldol reaction [J].

Nguyen, Quang Trung ;

Jeong, Jong Hwa .

POLYHEDRON, 2008, 27 (15) :3227-3230

[42] Synthesis and X-ray structure of a Cu(II) complex of N,N′-bis(2-pyridylmethylidene)-(R,R)-1,2-diaminocyclohexane and its catalytic application for asymmetric Henry reaction [J].

Nguyen, Quang Trung ;

Jeong, Jong Hwa .

POLYHEDRON, 2006, 25 (08) :1787-1790

[43] Syntheses, crystal structures and solid state thermochromic conversion of trans-1,2-diaminocyclohexane complexes of copper(II) perchlorate [J].

Pariya, C ;

Panneerselvan, K ;

Chung, CS ;

Lu, TH .

POLYHEDRON, 1998, 17 (15) :2555-2561

[44] Syntheses, crystal structures and solid state thermochromism of copper(II) complexes of trans-1,2-diaminocyclohexane [J].

Pariya, C ;

Liao, FL ;

Wang, SL ;

Chung, CS .

POLYHEDRON, 1998, 17 (04) :547-554

[45] Microcapsule enabled multicatalyst system [J].

Poe, Sarah L. ;

Kobaslija, Muris ;

McQuade, D. Tyler .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (49) :15586-15587

[46] BASIC CHARACTER OF RARE-EARTH-METAL ALKOXIDES - UTILIZATION IN CATALYTIC C-C BOND-FORMING REACTIONS AND CATALYTIC ASYMMETRIC NITROALDOL REACTIONS [J].

SASAI, H ;

SUZUKI, T ;

ARAI, S ;

ARAI, T ;

SHIBASAKI, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4418-4420

[47] Copper(II) complexes containing chiral substituted 2-(4-isopropyl-4-methyl-4,5-dihydro-1H-imidazol-5-one-2-yl)pyridine ligands:: Synthesis, X-ray structural studies and asymmetric catalysis [J].

Sedlak, Milos ;

Drabina, Pavel ;

Keder, Roman ;

Hanusek, Jiri ;

Cisarova, Ivana ;

Ruzicka, Ales .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (12) :2623-2630

[48] DIASTEREOSELECTIVE SYNTHESIS OF NITROALDOL DERIVATIVES [J].

SEEBACH, D ;

BECK, AK ;

MUKHOPADHYAY, T ;

THOMAS, E .

HELVETICA CHIMICA ACTA, 1982, 65 (04) :1101-1133

[49] Synthesis, characterisation and crystal structure of a 1,4-diazacycloheptane complex of copper(II) [J].

Sen, S ;

Saha, MK ;

Mitra, S ;

Edwards, AJ ;

Clegg, W .

POLYHEDRON, 2000, 19 (15) :1881-1885

[50]

Trost BM, 2002, ANGEW CHEM INT EDIT, V41, P861, DOI 10.1002/1521-3773(20020301)41:5<861::AID-ANIE861>3.0.CO

← 1 2 3 4 5 6 →