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Related Concept Videos

Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

11.8K
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...
11.8K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.2K
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...
3.2K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.6K
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.
7.6K
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

4.3K
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...
4.3K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

8.3K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
8.3K
Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

7.7K
The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
7.7K

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Updated: May 29, 2025

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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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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Electrocatalytic Alkene Hydrogenation/Deuteration.

Faxiang Bu1, Yuqi Deng1, Lijun Lu1

  • 1College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, P. R. China.

Journal of the American Chemical Society
|February 4, 2025
PubMed
Summary
This summary is machine-generated.

This study presents a universal electrocatalytic method for alkene reduction using water as a hydrogen source, avoiding hazardous high-pressure hydrogen gas. This green chemistry approach offers high yields for various alkenes and complex molecules.

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Hydrogen Production and Utilization in a Membrane Reactor
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Hydrogen Production and Utilization in a Membrane Reactor
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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Electrochemistry

Background:

  • Traditional alkene reduction methods like stoichiometric reductants and catalytic hydrogenation pose environmental and safety concerns due to waste generation and high-pressure hydrogen gas.
  • There is a need for sustainable and safer alternatives for alkene reduction in organic synthesis.

Purpose of the Study:

  • To develop a universal, environmentally friendly method for the electrocatalytic hydrogenation and deuteration of alkenes.
  • To utilize water (H2O) and heavy water (D2O) as sustainable sources for hydrogen and deuterium, respectively, under ambient conditions.

Main Methods:

  • Electrocatalytic reduction of alkenes using modified electrodes.
  • Generation of active metal hydride (M-H) and metal deuteride (M-D) species via electrolysis of H2O/D2O on modified electrodes.
  • Ambient temperature and pressure conditions, avoiding the need for H2 or D2 gas.

Main Results:

  • Successful reduction and deuteration of a wide range of alkenes, including mono-, di-, tri-, and tetra-substituted, electron-donating/withdrawing, and those with other reducible functional groups.
  • High yields (up to 99%) achieved for 85 examples, including complex natural products and drugs.
  • Excellent Faraday efficiency reaching 84% and a significant decrease in catalytic metal loading to less than 0.01 mol %.

Conclusions:

  • The developed electrocatalytic method provides a safe, efficient, and versatile approach for alkene hydrogenation and deuteration.
  • This method offers a sustainable alternative to traditional reduction techniques, minimizing waste and safety hazards.
  • The low catalyst loading and high efficiency make this a promising technique for both academic research and industrial applications.