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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...

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.

Properties of Organometallic Compounds

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

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 stereochemistry.

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

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Examining Metal Identity and Proximity Effects on Acetylene Hydrogenation with Azolate-Based MOFs.

Seryeong Lee^1,2, Milad Ahmadi Khoshooei¹, Xiaoliang Wang¹

¹Department of Chemistry and International Institute for Nanotechnology (IIN), Northwestern University, Evanston, Illinois 60208, United States.

ACS Applied Materials & Interfaces

|December 5, 2025

Summary

Metal-organic frameworks (MOFs) show promise for improving liquid organic hydrogen carrier (LOHC) catalysts. This study explores Ni- and Co-based MOFs, finding that coordination environment influences acetylene hydrogenation performance.

Keywords:

coordination environment hydrogenation isosteric heat of adsorption liquid organic hydrogen carriers metal−organic frameworks single-site catalysts

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Published on: October 10, 2013

Area of Science:

Materials Science
Catalysis
Chemical Engineering

Background:

Liquid organic hydrogen carriers (LOHCs) are essential for hydrogen storage and transport.
Existing LOHC catalysts suffer from slow hydrogenation kinetics, hindering their practical application.
Metal-organic frameworks (MOFs) offer tunable structures for designing advanced catalysts.

Purpose of the Study:

To investigate the impact of metal identity and coordination environment on MOF catalyst performance for acetylene hydrogenation.
To compare the catalytic activity and selectivity of Ni- and Co-based azolate MOFs with different node structures (single-site vs. chain-type).

Main Methods:

Synthesis and characterization of Ni- and Co-based azolate MOFs (MFU-4l-OH and M(OH)₂BBTA) using techniques like PXRD, SEM, ICP-OES, and XPS.
Evaluation of acetylene hydrogenation activity and selectivity under steady-state conditions.
Isosteric heat of adsorption (Q_st) measurements to assess product binding.

Main Results:

Ni- and Co-based MFU-4l-OH MOFs exhibited higher turnover frequencies (TOFs) for acetylene hydrogenation compared to their BBTA analogues.
Co-based MOFs, particularly Co₂(OH)₂-BBTA, demonstrated enhanced selectivity towards ethane.
The BBTA framework showed stronger binding of hydrogenation products (ethylene and ethane) than the MFU-4l framework.

Conclusions:

The metal identity and coordination environment within MOFs significantly influence acetylene hydrogenation activity and selectivity.
These findings provide valuable design principles for developing next-generation LOHC hydrogenation catalysts with improved performance.
Tailoring MOF structures can optimize the kinetics and selectivity of LOHC dehydrogenation/hydrogenation processes.