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Related Concept Videos

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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 Hydrogenation02:13

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

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.
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

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...
Heterogeneous Catalysis01:22

Heterogeneous Catalysis

Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...
Fast Reactions01:27

Fast Reactions

Fast reactions occurring in times shorter than the time needed to mix reactants pose a unique challenge for investigation. In a liquid-phase continuous-flow system, reactants A and B are swiftly pushed into the mixing chamber, where mixing occurs within 1 ms. The reaction mixture then flows through an observation tube, and one measures light absorption to determine species concentrations at various points of the tube. This method is most appropriate when relatively large volumes of reactants...

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Updated: May 24, 2026

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
12:08

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

Published on: June 24, 2022

Continuous-flow catalytic asymmetric hydrogenations: Reaction optimization using FTIR inline analysis.

Magnus Rueping1, Teerawut Bootwicha, Erli Sugiono

  • 1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany.

Beilstein Journal of Organic Chemistry
|March 17, 2012
PubMed
Summary
This summary is machine-generated.

Continuous-flow microreactors enable efficient asymmetric organocatalytic hydrogenation of various heterocycles. This method provides high yields and excellent enantioselectivities for valuable chemical products.

Keywords:
Brønsted acidHantzsch dihydropyridineIR spectroscopyasymmetric reductionbinolphosphoric acidreal-time analysis

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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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Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling
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Optimization of the Ugi Reaction Using Parallel Synthesis and Automated Liquid Handling

Published on: November 11, 2008

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Chemical Engineering

Background:

  • Asymmetric organocatalytic hydrogenation is crucial for synthesizing chiral molecules.
  • Continuous-flow microreactor technology offers advantages in reaction control and scalability.
  • Efficient methods for hydrogenating nitrogen-containing heterocycles are in demand.

Purpose of the Study:

  • To develop an asymmetric organocatalytic hydrogenation method using continuous-flow microreactors.
  • To investigate the hydrogenation of benzoxazines, quinolines, quinoxalines, and 3H-indoles.
  • To optimize reaction parameters for high yield and enantioselectivity.

Main Methods:

  • Utilized continuous-flow microreactors for asymmetric organocatalytic hydrogenation.
  • Employed an inline ReactIR flow cell for real-time reaction monitoring.
  • Systematically optimized reaction conditions including catalyst loading, temperature, and flow rates.

Main Results:

  • Successfully hydrogenated benzoxazines, quinolines, quinoxalines, and 3H-indoles.
  • Achieved high yields for the desired hydrogenated products.
  • Obtained excellent enantioselectivities in the asymmetric reductions.

Conclusions:

  • The developed continuous-flow microreactor system is effective for asymmetric organocatalytic hydrogenation.
  • Inline reaction monitoring facilitates rapid optimization of complex catalytic processes.
  • This approach offers a scalable and efficient route to enantiomerically enriched heterocyclic compounds.