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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...
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...
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.
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone.
When dissolved in liquid ammonia, an alkali metal, such as sodium, dissociates into a...
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...

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Lanthanum(III) catalysts for highly efficient and chemoselective transesterification.

Manabu Hatano1, Kazuaki Ishihara

  • 1Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan.

Chemical Communications (Cambridge, England)
|January 18, 2013
PubMed
Summary

Lanthanum(III) catalysts enable efficient transesterification of diverse esters and alcohols, including challenging substrates like carbamates and tertiary alcohols. This practical method simplifies synthesis and purification for pharmaceutical and material applications.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Esterification and transesterification are vital reactions in organic synthesis.
  • Existing catalytic methods often have limitations in substrate scope and practicality.
  • Development of efficient, selective, and broadly applicable transesterification catalysts is needed.

Purpose of the Study:

  • To develop highly active and practical lanthanum(III) catalysts for transesterification.
  • To expand the substrate scope of catalytic transesterification to include less reactive esters and various alcohols.
  • To establish a simplified and efficient synthetic route for ester production.

Main Methods:

  • Utilizing ligand-free and ligand-assisted lanthanum(III) complexes as catalysts.
  • In situ preparation of dinuclear lanthanum(III) catalysts and lanthanum(III) nitrate alkoxides.
  • Employing methyl carboxylates, ethyl acetate, dimethyl carbonate, and methyl carbamates as substrates.
  • Reacting with primary, secondary, and tertiary alcohols under optimized conditions.

Main Results:

  • Developed highly active dinuclear La(III) and lanthanum(III) nitrate alkoxide catalysts.
  • Achieved efficient transesterification of methyl carboxylates, ethyl acetate, dimethyl carbonate, and methyl carbamates.
  • Demonstrated effectiveness with primary, secondary, and tertiary alcohols, including challenging substrates.
  • Enabled non-epimerized transesterification of chiral esters under reflux conditions.
  • Obtained colorless esters with simplified work-up and purification.

Conclusions:

  • Lanthanum(III) catalysts offer a versatile and practical solution for broad transesterification applications.
  • The developed catalytic systems overcome limitations of conventional methods, enabling synthesis with diverse alcohols.
  • These methods provide an atom-economical and chemoselective route to valuable ester products for various industries.