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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...

Regioselectivity of Electrophilic Additions-Peroxide Effect

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

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Related Experiment Video

Updated: Apr 15, 2026

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

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Published on: June 24, 2022

Selectivity control in Pt-catalyzed cinnamaldehyde hydrogenation.

Lee J Durndell¹, Christopher M A Parlett¹, Nicole S Hondow²

¹European Bioenergy Research Institute, Aston University, Birmingham B4 7ET, UK.

Scientific Reports

|March 25, 2015

Summary

Platinum nanoparticle size and support polarity control chemoselective hydrogenation of aromatic aldehydes. Larger nanoparticles and higher pressures favor carbonyl hydrogenation, while support polarity influences reactant orientation for enhanced selectivity.

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Area of Science:

Catalysis
Nanomaterials
Organic Chemistry

Background:

Chemoselectivity is crucial for targeted chemical modifications.
Hydrogenation of aldehydes is a fundamental organic transformation.

Purpose of the Study:

To elucidate factors controlling the chemoselective liquid-phase hydrogenation of cinnamaldehyde and related benzylic aldehydes over platinum (Pt) nanoparticles.
To understand the influence of nanoparticle structure and electronic properties on reaction outcomes.

Main Methods:

Kinetic mapping to analyze reaction mechanisms.
In situ vibrational spectroscopies to study surface interactions.
Systematic variation of platinum nanoparticle size, precursor, support architecture, and hydrogen pressure.

Main Results:

Cinnamaldehyde hydrogenation over metallic platinum is structure-insensitive regarding turnover frequency.
Selectivity towards cinnamyl alcohol is highly structure-sensitive, favoring C=O over C=C hydrogenation with larger nanoparticles and higher pressures.
Support polarity enhances C=O hydrogenation by influencing cinnamaldehyde reorientation, a phenomenon observed for other aromatic aldehydes.

Conclusions:

Nanoparticle size and support polarity are key tunable parameters for controlling chemoselectivity in aromatic aldehyde hydrogenation.
Understanding structure-reactivity relationships enables rational catalyst design for selective chemical transformations.