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Related Concept Videos

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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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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...
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.9K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.0K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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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...
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Reversible C-C bond formation using palladium catalysis.

Austin D Marchese1, Bijan Mirabi1, Colton E Johnson1

  • 1Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, Toronto, Ontario, Canada.

Nature Chemistry
|March 18, 2022
PubMed
Summary
This summary is machine-generated.

This study demonstrates reversible carbon-carbon bond formation using palladium catalysis. Both cis and trans diastereomers of neopentyl iodides convert to a common product, revealing key insights into reaction reversibility.

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Area of Science:

  • Organic Chemistry
  • Catalysis

Background:

  • Chemical reactions are fundamentally reversible.
  • Observing reversible C-C bond cleavage in transition metal-catalyzed reactions is challenging.

Purpose of the Study:

  • To investigate the reversibility of C-C bond formation using palladium catalysis.
  • To explore the mechanism of reversible C-C bond formation with diastereomeric neopentyl iodides.

Main Methods:

  • Palladium-catalyzed reactions using diastereomeric neopentyl iodides.
  • Experimental and computational studies to probe reaction mechanisms.
  • Investigation of electronic and steric effects on C-C bond cleavage.

Main Results:

  • Both cis and trans neopentyl iodide diastereomers were converted to a common product under identical palladium-catalyzed conditions.
  • The study elucidated key factors influencing reversible C-C bond formation.

Conclusions:

  • Palladium catalysis enables reversible C-C bond formation.
  • Understanding reaction reversibility is crucial for developing efficient catalytic processes.