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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...

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 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...

Catalysis

Catalysis

The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.

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.

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...

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Updated: Jun 8, 2025

Hydrogen Production and Utilization in a Membrane Reactor

Hydrogen Production and Utilization in a Membrane Reactor

Published on: March 10, 2023

Exploiting hydrogenases for biocatalytic hydrogenations.

Daria Sokolova¹, Kylie A Vincent¹

¹Department of Chemistry, University of Oxford, Inorganic Chemistry Laboratory, South Parks Road, Oxford, OX1 3QR, UK. kylie.vincent@chem.ox.ac.uk.

Chemical Communications (Cambridge, England)

|November 8, 2024

Summary

Hydrogenase enzymes enable clean hydrogen fuel (H2) applications in biotechnology. This review highlights their use in driving hydrogenation reactions, paving the way for industrial applications.

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Area of Science:

Biotechnology
Biocatalysis
Enzyme engineering

Background:

Hydrogenase enzymes efficiently activate H2, offering potential as clean reductants in biotechnology.
Site-separated reactivity is crucial for many catalytic processes, including those driven by hydrogenases.

Purpose of the Study:

To review the use of hydrogenase enzymes in driving hydrogenation reactions.
To highlight contributions to the field of biocatalytic hydrogenations.
To discuss the industrial biotechnology applications and future opportunities for hydrogenases.

Main Methods:

Review of examples utilizing hydrogenase enzymes for hydrogenation reactions in solution and on conductive supports.
Focus on NiFe hydrogenases, with brief mention of FeFe hydrogenases.
Analysis of coupled redox reactions enabling hydrogenation via H2 oxidation and linked reduction.

Main Results:

Hydrogenase enzymes successfully drive native and non-native hydrogenation reactions.
Coupled redox reactions, involving H2 oxidation and linked reduction, are key to these processes.
Productivities and potential industrial applications of biocatalytic hydrogenations were discussed.

Conclusions:

Hydrogenase-driven hydrogenation reactions show significant promise for industrial biotechnology.
Scaling hydrogenase production and further research offer future opportunities.
The development of site-separated reactivity parallels advancements in heterogeneous catalysis.