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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

14.1K
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...
14.1K
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

5.9K
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...
5.9K
Hydrogen Bonds00:26

Hydrogen Bonds

133.9K
Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
133.9K
Hydrogen Bonds01:04

Hydrogen Bonds

14.8K
A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.9K
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 Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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.
9.1K

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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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Catalytic Transfer Hydrogenation Using Biomass as Hydrogen Source.

Srimanta Manna1,2, Andrey P Antonchick1,2,3

  • 1Abteilung Chemische Biologie, Max-Planck-Institut für Molekulare Physiologie, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany.

Chemsuschem
|August 4, 2018
PubMed
Summary

Biomass can now directly act as a reducing agent in hydrogenation reactions. This new method uses biomass-derived compounds for efficient and stereoselective reduction of various chemical groups.

Keywords:
biomasscarbohydratesgreen chemistryhydrogenationrhodium

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Area of Science:

  • Green Chemistry
  • Organic Synthesis
  • Catalysis

Background:

  • Hydrogenation is a crucial organic reaction.
  • Current methods often rely on non-renewable resources.
  • Developing sustainable alternatives is essential.

Purpose of the Study:

  • To introduce a direct method for using biomass-derived chemicals in hydrogenation.
  • To explore the use of biomass as a reducing reagent.
  • To achieve stereoselective and regioselective hydrogenation.

Main Methods:

  • Utilized biomass-derived compounds (carbohydrates, starch, lignin) as reducing agents.
  • Employed a novel transition metal catalytic system.
  • Varied reaction conditions to control stereoselectivity and regioselectivity.

Main Results:

  • Demonstrated high yields in the reduction of alkynes, alkenes, and carbonyl groups.
  • Achieved stereoselective hydrogenation of various substrates.
  • Established regioselective control to access different stereoisomers.

Conclusions:

  • Developed an operationally simple method for biomass utilization in hydrogenation.
  • Showcased the potential of biomass as a sustainable reducing reagent.
  • This work offers a straightforward application of biomass in chemical synthesis.