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Related Concept Videos

Catalysis02:50

Catalysis

31.5K
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.
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Heterogeneous Catalysis01:22

Heterogeneous Catalysis

48
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...
48
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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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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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.
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Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

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Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Catalysis with Chalcogen Bonds.

Sebastian Benz1, Javier López-Andarias1, Jiri Mareda1

  • 1Department of Organic Chemistry, University of Geneva, Geneva, Switzerland.

Angewandte Chemie (International Ed. in English)
|December 17, 2016
PubMed
Summary
This summary is machine-generated.

New catalysts utilize chalcogen bonds for precision catalysis in nonpolar solvents, achieving over 1000x rate enhancements in transfer hydrogenation. These bonds offer unique directionality and hydrophobicity for improved catalytic activity.

Keywords:
chalcogen bondsdithienothiopheneshomogeneous catalysistransfer hydrogenation

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Area of Science:

  • Supramolecular Chemistry
  • Catalysis
  • Organic Chemistry

Background:

  • Hydrogen bonds are crucial in catalysis but have limitations in apolar solvents.
  • Chalcogen bonds offer similar strength but enhanced directionality and hydrophobicity.
  • Developing novel catalysts for precision chemical transformations is an ongoing challenge.

Purpose of the Study:

  • To introduce and investigate catalysts operating via chalcogen bonds.
  • To demonstrate the efficacy of chalcogen bonds in enhancing catalytic reactions.
  • To identify privileged structural motifs for effective chalcogen bond catalysis.

Main Methods:

  • Catalyst design utilizing dithieno[3,2-b;2',3'-d]thiophenes (DTTs) and cyclopentadithiazole-4-ones.
  • Experimental investigation of transfer hydrogenation of quinolines and imines.
  • Computational analysis of anion binding energies and reaction mechanisms.

Main Results:

  • Achieved rate enhancements exceeding 1000-fold in transfer hydrogenation reactions.
  • Demonstrated correlation between catalytic activity, electronic properties (σ-holes), and structural features (bite angle).
  • Identified DTT diimides and cyclopentadithiazole-4-ones as effective scaffolds for chalcogen bond catalysis.

Conclusions:

  • Chalcogen bonds represent a powerful tool for precision catalysis, particularly in apolar media.
  • The developed catalysts exhibit superior activity compared to traditional systems.
  • Structural optimization of chalcogen-bonding motifs can significantly improve catalytic performance.