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Related Concept Videos

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.
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...
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...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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Updated: May 14, 2026

Synthesis and Testing of Supported Pt-Cu Solid Solution Nanoparticle Catalysts for Propane Dehydrogenation
10:19

Synthesis and Testing of Supported Pt-Cu Solid Solution Nanoparticle Catalysts for Propane Dehydrogenation

Published on: July 18, 2017

Introducing copper as catalyst for oxidative alkane dehydrogenation.

Ana Conde1, Laia Vilella, David Balcells

  • 1Laboratorio de Catálisis Homogénea, Departamento de Química y Ciencia de los Materiales, Unidad Asociada al CSIC, Centro de Investigación en Química Sostenible, Universidad de Huelva, Campus de El Carmen, 21007 Huelva, Spain.

Journal of the American Chemical Society
|February 16, 2013
PubMed
Summary
This summary is machine-generated.

Copper catalysts with trispyrazolylborate ligands facilitate n-hexane and cycloalkane dehydrogenation using hydrogen peroxide. This novel process yields alcohols and ketones, with minor alkene formation, distinct from typical Fenton-like reactions.

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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether
09:21

Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether

Published on: August 17, 2019

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Synthesis and Testing of Supported Pt-Cu Solid Solution Nanoparticle Catalysts for Propane Dehydrogenation
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Synthesis and Testing of Supported Pt-Cu Solid Solution Nanoparticle Catalysts for Propane Dehydrogenation

Published on: July 18, 2017

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether
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Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether

Published on: August 17, 2019

Area of Science:

  • Catalysis
  • Organometallic Chemistry
  • Oxidation Reactions

Background:

  • Hydrogen peroxide is a versatile oxidant in catalytic processes.
  • Copper complexes are effective catalysts for various organic transformations.
  • Trispyrazolylborate ligands stabilize metal centers and influence reactivity.

Purpose of the Study:

  • To investigate the catalytic dehydrogenation of n-hexane and cycloalkanes using copper complexes and hydrogen peroxide.
  • To elucidate the reaction mechanism, including the nature of the active species and key intermediates.
  • To explore the selectivity towards oxidation and dehydrogenation products.

Main Methods:

  • Catalytic reactions using copper complexes with trispyrazolylborate ligands and hydrogen peroxide.
  • Experimental analysis to identify reaction products and exclude radical mechanisms.
  • Density Functional Theory (DFT) studies to model the reaction pathway and active species.

Main Results:

  • Catalytic dehydrogenation of n-hexane and cycloalkanes to n-hexene and cycloalkenes was achieved.
  • The reaction predominantly yielded oxidation products (alcohols and ketones) with minor amounts of alkenes.
  • DFT studies indicated a copper-oxo species as the active initiator, proceeding via H abstraction.
  • Spin crossover from triplet to singlet state was crucial for catalyst recovery and product distribution.

Conclusions:

  • A novel catalytic system for hydrocarbon functionalization using hydrogen peroxide was developed.
  • The mechanism involves a copper-oxo species and spin crossover, differentiating it from Fenton-like processes.
  • The study provides a comprehensive mechanistic proposal supported by experimental and computational evidence.