Mild and Selective Catalytic Hydrogenation of the C=C Bond in α,β-Unsaturated Carbonyl Compounds Using Supported Palladium Nanoparticles

被引：37

作者：

Nagendiran, Anuja ^{[1
,2
]}

Pascanu, Vlad ^{[1
,2
]}

Gomez, Antonio Bermejo ^{[1
,2
,4
]}

Miera, Greco Gonzalez ^{[1
,2
]}

Tai, Cheuk-Wai ^{[3
]}

Verho, Oscar ^{[1
,2
]}

Martin-Matute, Belen ^{[1
,2
]}

Backvall, Jan-E. ^{[1
,2
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden

[2] Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, Arrhenius Lab, S-10691 Stockholm, Sweden

[3] Stockholm Univ, Dept Mat & Environm Chem, S-10691 Stockholm, Sweden

[4] Karolinska Inst, AstraZeneca Translat Sci Ctr, S-17165 Stockholm, Sweden

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 21期

基金：

瑞典研究理事会;

关键词：

heterogeneous catalysis; mesocellular foam; metal-organic framework; palladium nanoparticles; selective hydrogenation; PD-AT-MOF; FUNCTIONALIZED MESOCELLULAR FOAM; METAL-ORGANIC FRAMEWORKS; CROSS-COUPLING REACTION; CHEMOSELECTIVE HYDROGENATION; EFFICIENT; CINNAMALDEHYDE; NANOPALLADIUM; ENZYME;

D O I：

10.1002/chem.201600878

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chemoselective reduction of the C=C bond in a variety of alpha,beta-unsaturated carbonyl compounds using supported palladium nanoparticles is reported. Three different heterogeneous catalysts were compared using 1 atm of H-2 : 1) nano-Pd on a metal-organic framework (MOF: Pd-0-MIL-101-NH2(Cr)), 2) nano-Pd on a siliceous mesocellular foam (MCF: Pd-0-AmP-MCF), and 3) commercially available palladium on carbon (Pd/C). Initial studies showed that the Pd@MOF and Pd@MCF nanocatalysts were superior in activity and selectivity compared to commercial Pd/C. Both Pd-0-MIL-101-NH2(Cr) and Pd-0-AmP-MCF were capable of delivering the desired products in very short reaction times (1090 min) with low loadings of Pd (0.5-1 mol%). Additionally, the two catalytic systems exhibited high recyclability and very low levels of metal leaching.

引用

页码：7184 / 7189

页数：6

共 36 条

[1] Babu V., 2013, BIOFUEL PRODUCTION
[2] Benvenuto M. A., 2015, IND CHEM ADV STUDENT
[3] Direct covalent post-synthetic chemical modification of Cr-MIL-101 using nitrating acid
Bernt, Stephan
Guillerm, Vincent
Serre, Christian
Stock, Norbert
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (10) : 2838 - 2840
[4] A General Suzuki Cross-Coupling Reaction of Heteroaromatics Catalyzed by Nanopalladium on Amino-Functionalized Siliceous Mesocellular Foam
Bratt, Emma
Verho, Oscar
Johansson, Magnus J.
Backvall, Jan-Erling
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09) : 3946 - 3954
[5] Influence of the Base on Pd@MIL-101-NH2(Cr) as Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction
Carson, Fabian
Pascanu, Vlad
Gomez, Antonio Bermejo
Zhang, Yi
Platero-Prats, Ana E.
Zou, Xiaodong
Martin-Matute, Belen
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (30) : 10896 - 10902
[6] One-pot synthesis of Pd@MOF composites without the addition of stabilizing agents
Chen, Liyu
Chen, Huirong
Li, Yingwei
[J]. CHEMICAL COMMUNICATIONS, 2014, 50 (94) : 14752 - 14755
[7] Metal-organic frameworks: versatile heterogeneous catalysts for efficient catalytic organic transformations
Chughtai, Adeel H.
Ahmad, Nazir
Younus, Hussein A.
Laypkov, A.
Verpoort, Francis
[J]. CHEMICAL SOCIETY REVIEWS, 2015, 44 (19) : 6804 - 6849
[8] Collins G., 2014, Angew. Chem, V126, P4226
[9] The Origin of Shape Sensitivity in Palladium-Catalyzed Suzuki-Miyaura Cross Coupling Reactions
Collins, Gillian
Schmidt, Michael
Dwyer, Colm O.
Holmes, Justin D.
McGlacken, Gerard P.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (16) : 4142 - 4145
[10] Catalysis by metal nanoparticles embedded on metal-organic frameworks
Dhakshinamoorthy, Amarajothi
Garcia, Hermenegildo
[J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (15) : 5262 - 5284

← 1 2 3 4 →