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Reduction of Alkenes: Catalytic Hydrogenation

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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.
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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.
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Introduction
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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...

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Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
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Related Experiment Video

Updated: Mar 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

Imino Transfer Hydrogenation Reductions.

¹The Department of Chemistry, Warwick University, Coventry, CV4 7AL, UK. m.wills@warwick.ac.uk.

Topics in Current Chemistry (Cham)

|August 31, 2016

Summary

This summary is machine-generated.

This review summarizes recent advances in transfer hydrogenation of C=N bonds, focusing on asymmetric methods and catalysts like Ru/TsDPEN and iridium complexes for synthesizing chiral amines.

Keywords:

Amine Asymmetric Hydrogenation Imine Reduction Transfer

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Area of Science:

Organic Chemistry
Catalysis
Asymmetric Synthesis

Background:

Transfer hydrogenation is a key method for reducing imine (C=N) bonds.
Asymmetric transfer hydrogenation (ATH) enables chiral amine synthesis.
Recent advancements have focused on highly active and selective catalysts.

Purpose of the Study:

To review recent developments in transfer hydrogenation of C=N bonds, particularly asymmetric transformations.
To highlight the Ru/TsDPEN and iridium-based catalyst systems.
To discuss diastereoselective methods and novel protein-based approaches.

Main Methods:

Focus on literature from the last 10 years, with earlier work for context.
Detailed discussion of Ru/TsDPEN catalyzed asymmetric transfer hydrogenation.
Exploration of iridium-based catalysts for imine reduction.
Analysis of diastereoselective reduction strategies.
Review of protein-guided asymmetric reduction methodologies.

Main Results:

Ru/TsDPEN catalysts are effective for asymmetric transfer hydrogenation.
Iridium catalysts show high activity in imine reduction.
Diastereoselective methods provide access to chiral amines.
Protein engineering allows for controlled asymmetric reduction.

Conclusions:

Significant progress has been made in asymmetric transfer hydrogenation of C=N bonds.
Novel catalyst systems and methodologies continue to emerge.
Applications in synthesizing medically valuable molecules are expanding.