Cu(II)-Azabis(oxazoline) Complexes Immobilized on Magnetic Co/C Nanoparticles: Kinetic Resolution of 1,2-Diphenylethane-1,2-diol under Batch and Continuous-Flow Conditions

被引：88

作者：

Schaetz, Alexander ^{[1
]}

Grass, Robert N. ^{[2
]}

Kainz, Quirin ^{[1
]}

Stark, Wendelin J. ^{[2
]}

Reiser, Oliver ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany

[2] Swiss Fed Inst Technol, Inst Chem & Bioingenieurwissensch, Dept Chem & Angew Biowissensch, CH-8093 Zurich, Switzerland

来源：

CHEMISTRY OF MATERIALS | 2010年 / 22卷 / 02期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; POLYMER-SUPPORTED REAGENTS; ORGANIC-SYNTHESIS; SOLID-PHASE; CATALYST; LIGANDS; BIS(OXAZOLINE); NANOCAPSULES; EFFICIENCY; SCAVENGERS;

D O I：

10.1021/cm9019099

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：

Carbon coated cobalt nanoparticles were tagged with azabis(oxazoline)-copper(II) complexes utilizing a copper(I)-catalyzed azide/alkyne cycloaddition (CuAAC) reaction, and the efficacy of the resulting nanomagnetic catalyst was tested in the kinetic resolution of racemic 1,2-diphenylethane-1,2-diol via asymmetric monobenzoylation. The novel semiheterogeneous catalyst was examined under batch conditions and in a continuous flow-type reactor. The extremely high ferromagnetism of the cobalt cores not only facilitates the recycling of the nanobeads via magnetic decantation in the batch reactions but also enables it novel continuous flow-reactor design: This further allowed efficient agitation and containment of the particles to occur without the need for sophisticated separation strategies Such its nanofiltration.

引用

页码：305 / 310

页数：6

共 65 条

[1] Metal supported on dendronized magnetic nanoparticles: Highly selective hydroformylation catalysts [J].

Abu-Reziq, R ;

Alper, H ;

Wang, DS ;

Post, ML .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :5279-5282

[2] Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides [J].

Annis, DA ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4147-4154

[3] Tailored conductivity behavior in nanocrystalline nickel ferrite [J].

Baruwati, B ;

Reddy, KM ;

Manorama, SV ;

Singh, RK ;

Parkash, O .

APPLIED PHYSICS LETTERS, 2004, 85 (14) :2833-2835

[4] 'Click' chemistry in polymer and materials science [J].

Binder, Wolfgang H. ;

Sachsenhofer, Robert .

MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (01) :15-54

[5] Azide/alkyne-"click" reactions: Applications in material science and organic synthesis [J].

Binder, Wolfgang H. ;

Kluger, Christian .

CURRENT ORGANIC CHEMISTRY, 2006, 10 (14) :1791-1815

[6] Pybox monolithic miniflow reactors for continuous asymmetric cyclopropanation reaction under conventional and supercritical conditions [J].

Burguete, M. I. ;

Cornejo, A. ;

Garcia-Verdugo, E. ;

Gil, Maria J. ;

Luis, S. V. ;

Mayoral, J. A. ;

Martinez-Merino, V. ;

Sokolova, M. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (12) :4344-4350

[7] Polymer-supported bis(oxazolines) and related systems:: Toward new heterogeneous enantioselective catalysts [J].

Burguete, MI ;

Fraile, JM ;

García-Verdugo, E ;

Luis, SV ;

Martínez-Merino, V ;

Mayoral, JA .

INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2005, 44 (23) :8580-8587

[8]

Cybulski A., 1998, STRUCTURED CATALYSIS

[9]

Dalaigh C. O., 2007, ANGEW CHEM, V119, P4407, DOI DOI 10.1002/ANGE.200605216

[10] C2-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis [J].

Desimoni, Giovanni ;

Faita, Giuseppe ;

Jorgensen, Karl Anker .

CHEMICAL REVIEWS, 2006, 106 (09) :3561-3651

← 1 2 3 4 5 6 7 →