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Related Concept Videos

Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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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 Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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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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Formation of Pyramidal Palladium Enhanced by B(C6F5)3 Additive Enabling Selective Alkene Monoisomerization.

Paul D Miller1, Trandon A Bender1

  • 1Department of Chemistry and Biochemistry, Old Dominion University, 4501 Elkhorn Ave, Norfolk, Virginia 23529, United States.

ACS Omega
|January 1, 2026
PubMed
Summary
This summary is machine-generated.

A new method uses a Lewis acid to create palladium nanoparticles for selective alkene monoisomerization. This catalyst is robust and can be made using industrial waste, offering a sustainable approach to isomerization chemistry.

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Area of Science:

  • Catalysis
  • Materials Science
  • Organic Chemistry

Background:

  • Palladium nanoparticles are valuable catalysts.
  • Efficient synthesis of palladium nanoparticles is crucial.
  • Alkene isomerization is an important chemical transformation.

Purpose of the Study:

  • To develop a novel method for palladium nanoparticle synthesis.
  • To investigate the catalytic activity of these nanoparticles in alkene isomerization.
  • To explore sustainable reductants for nanoparticle formation.

Main Methods:

  • Reduction of Pd-(cod)-Cl2 using Et3SiH in the presence of tris-(pentafluorophenyl)-borane.
  • Characterization of the resulting palladium nanoparticles.
  • Testing the catalytic performance in selective monoisomerization of linear alkenes.
  • Evaluation of catalyst tolerance to various functional groups.
  • Utilizing poly-(methylhydro)-siloxane as an alternative reductant.

Main Results:

  • Successfully synthesized palladium nanoparticles using a Lewis acid-mediated reduction.
  • Demonstrated the capability of these nanoparticles for selective monoisomerization of linear alkenes.
  • Confirmed the heterogeneous catalyst's tolerance to a wide range of functional groups.
  • Showcased the use of poly-(methylhydro)-siloxane as a viable, sustainable reductant for similar chemistry.

Conclusions:

  • The Lewis acid-mediated synthesis provides an effective route to palladium nanoparticles.
  • These nanoparticles serve as efficient and selective heterogeneous catalysts for alkene monoisomerization.
  • The use of industrial waste as a reductant offers a greener alternative for catalyst preparation.