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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.7K
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.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric 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.
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...
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Reduction of Alkenes: Catalytic Hydrogenation02:13

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.
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...
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Catalysis02:50

Catalysis

26.9K
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.
26.9K
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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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...
4.5K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

18.0K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Related Experiment Video

Updated: Jun 25, 2025

Ethylene Polymerizations Using Parallel Pressure Reactors and a Kinetic Analysis of Chain Transfer Polymerization
07:28

Ethylene Polymerizations Using Parallel Pressure Reactors and a Kinetic Analysis of Chain Transfer Polymerization

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Alkene Isomerization Using a Heterogeneous Nickel-Hydride Catalyst.

Alison Sy-Min Chang1, Melanie A Kascoutas1, Quinn P Valentine1

  • 1Department of Chemistry and Biochemistry, University of Oregon, Eugene, Oregon 97403, United States.

Journal of the American Chemical Society
|May 21, 2024
PubMed
Summary

A novel heterogeneous nickel catalyst supported on sulfated zirconia (SZO300) demonstrates high activity and selectivity for alkene isomerization. This robust catalyst, made from Earth-abundant elements, overcomes the limitations of homogeneous and precious metal-based systems.

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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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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

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Area of Science:

  • Catalysis
  • Materials Science
  • Organic Chemistry

Background:

  • Homogeneous catalysts offer tunable selectivity but lack stability and recyclability.
  • Heterogeneous catalysts are robust but often lack active-site specificity and are difficult to improve.
  • Existing single-site heterogeneous catalysts use expensive precious metals and complex supports.

Purpose of the Study:

  • To develop a stable, recyclable, and highly active heterogeneous catalyst for alkene isomerization using Earth-abundant elements.
  • To overcome the decomposition issues of homogeneous nickel-hydride catalysts.
  • To achieve improved selectivity and broader functional group tolerance compared to existing systems.

Main Methods:

  • Immobilization of a nickel-based active site onto sulfated zirconia (SZO300).
  • Catalytic testing for alkene isomerization, hydroalkenylation, hydroboration, and hydrosilylation.
  • Kinetic studies to compare nickel and palladium catalysts.

Main Results:

  • The Ni/SZO300 catalyst exhibits high activity and selectivity for alkene isomerization, surpassing homogeneous and precious metal catalysts.
  • Decomposition issues of the homogeneous precursor are prevented by immobilization.
  • The catalyst demonstrates a broad scope of functional group tolerance and activity in other reactions.

Conclusions:

  • Sulfated zirconia is an effective support for creating robust and highly active heterogeneous catalysts from Earth-abundant metals.
  • The Ni/SZO300 system represents a significant advancement in alkene isomerization catalysis, offering a practical and sustainable alternative.
  • This heterogeneous catalyst shows potential for various important organic transformations beyond isomerization.