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

Anuja Nagendiran; Vlad Pascanu; Antonio Bermejo Gómez; Greco González Miera; Cheuk-Wai Tai; Oscar Verho; Belén Martín-Matute; Jan-E Bäckvall

doi:10.1002/chem.201600878

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

Chemistry. 2016 May 17;22(21):7184-9. doi: 10.1002/chem.201600878. Epub 2016 Apr 25.

Authors

Anuja Nagendiran¹, Vlad Pascanu¹, Antonio Bermejo Gómez^{1

2}, Greco González Miera¹, Cheuk-Wai Tai³, Oscar Verho⁴, Belén Martín-Matute⁵, Jan-E Bäckvall⁶

Affiliations

¹ Department of Organic Chemistry and, Berzelii Centre EXSELENT on Porous Materials, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden.
² AstraZeneca Translational Science Center at Karolinska Institute, 171 65, Stockholm, Sweden.
³ Department of Materials and Environmental Chemistry, Stockholm University, 106 91, Stockholm, Sweden.
⁴ Department of Organic Chemistry and, Berzelii Centre EXSELENT on Porous Materials, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden. [email protected].
⁵ Department of Organic Chemistry and, Berzelii Centre EXSELENT on Porous Materials, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden. [email protected].
⁶ Department of Organic Chemistry and, Berzelii Centre EXSELENT on Porous Materials, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden. [email protected].

PMID: 27111403
DOI: 10.1002/chem.201600878

Abstract

Chemoselective reduction of the C=C bond in a variety of α,β-unsaturated carbonyl compounds using supported palladium nanoparticles is reported. Three different heterogeneous catalysts were compared using 1 atm of H2 : 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 (10-90 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.

Keywords: heterogeneous catalysis; mesocellular foam; metal-organic framework; palladium nanoparticles; selective hydrogenation.

Publication types

Research Support, Non-U.S. Gov't