Asymmetric transfer hydrogenation of carbonyl compounds catalyzed by rhodium nanoparticles

被引：10

作者：

Nindakova, Lidiya O. ^{[1
]}

Badyrova, Nataliya M. ^{[1
]}

Smirnov, Vladimir V. ^{[1
]}

Kolesnikov, Sergey S. ^{[1
]}

机构：

[1] Irkutsk Natl Res Tech Univ, 83 Lermontov St, Irkutsk 664074, Russia

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2016年 / 420卷

关键词：

Transfer hydrogenation; Rhodium nanoparticle; Nanocatalysis; Optically active modifier; Enantioselectivity; HETEROGENEOUS ENANTIOSELECTIVE HYDROGENATION; METAL NANOCLUSTER STABILIZATION; MODIFIED PLATINUM CATALYSTS; ETHYL PYRUVATE; ARENE HYDROGENATION; ACID; NANOCATALYSIS; ACETOPHENONE; COMPLEXES; REDUCTION;

D O I：

10.1016/j.molcata.2016.04.007

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：

Transfer hydrogenation of acetophenone and methyl benzoylformate with 2-propanol has been studied on rhodium nanoparticles obtained by the reduction of rhodium(I) complexes in the presence of optically active compounds, including chiral diamine S,S-DIODMA, (4S,5S)-N-4,N-4,N-5,N-5,2,2-hexamethyl-4,5-bis-(aminomethylene)-1,3-dioxolane, quaternary diammonium salt (4S,5S)-(-)-N-1,N-4-dibenzyl-2,3-dihydroxy-N-1,N-1,N-4,N-4-tetramethylbutane-1,4-diammonium dichloride, and (8S,9R)-(-)-cinchonidine. Increasing the modifier to Rh ratio leads to an increase in the enantiomeric excess (ee) of the reaction products. The greatest ee values (43.8% for (R)-1-phenylethanol and 58.2% for the methyl ester of (R)-mandelic acid) were achieved at (8S,9R)-(-)-cinchonidine/Rh ratios of 9:1 and 3:1, respectively. (C) 2016 Elsevier B.V. All rights reserved.

引用

页码：149 / 158

页数：10

共 66 条

[1] Iridium Ziegler-Type Hydrogenation Catalysts Made from [(1,5-COD)Ir(μ-O2C8H15)]2 and AIEt3: Spectroscopic and Kinetic Evidence for the Irn Species Present and for Nanoparticles as the Fastest Catalyst [J].

Alley, William M. ;

Hamdemir, Isil K. ;

Wang, Qi ;

Frenkel, Anatoly I. ;

Li, Long ;

Yang, Judith C. ;

Menard, Laurent D. ;

Nuzzo, Ralph G. ;

Ozkar, Saim ;

Johnson, Kimberly A. ;

Finke, Richard G. .

INORGANIC CHEMISTRY, 2010, 49 (17) :8131-8147

[2]

Arx M.V., 2002, TOP CATAL, V19, P75, DOI DOI 10.1023/A:1013885300523

[3] Chiral diphosphite-modified rhodium(0) nanoparticles:: Catalyst reservoir for styrene hydroformylation [J].

Axet, M. Rosa ;

Castillon, Sergio ;

Claver, Carmen ;

Philippot, Karine ;

Lecante, Pierre ;

Chaudret, Bruno .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2008, (22) :3460-3466

[4] Reflections on chiral metal surfaces and their potential for catalysis [J].

Baiker, A .

CATALYSIS TODAY, 2005, 100 (1-2) :159-170

[5] Progress in asymmetric heterogeneous catalysis: Design of novel chirally modified platinum metal catalysts [J].

Baiker, A .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 115 (03) :473-493

[6] Transition state analogues - a guide for the rational design of enantioselective heterogeneous hydrogenation catalysts [J].

Baiker, A .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 163 (1-2) :205-220

[7] Emerging strategies in sustainable fine-chemical synthesis: asymmetric catalysis by metal nanoparticles [J].

Barbaro, Pierluigi ;

Dal Santo, Vladimiro ;

Liguori, Francesca .

DALTON TRANSACTIONS, 2010, 39 (36) :8391-8402

[8] Cinchona-modified platinum catalysts: From ligand acceleration to technical processes [J].

Blaser, Hans-Ulrich ;

Studer, Martin .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) :1348-1356

[9] Heterogeneous enantioselective hydrogenation of ethyl pyruvate catalyzed by cinchona-modified Pt catalysts: Effect of modifier structure [J].

Blaser, HU ;

Jalett, HP ;

Lottenbach, W ;

Studer, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12675-12682

[10] Enantioselective hydrogenation of alpha-ketoesters using cinchona modified platinum catalysts and related systems: A review [J].

Blaser, HU ;

Jalett, HP ;

Muller, M ;

Studer, M .

CATALYSIS TODAY, 1997, 37 (04) :441-463

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