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Related Concept Videos

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.
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...
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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...
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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.
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.

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Related Experiment Video

Updated: May 8, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

Published on: January 17, 2020

Catalyst-controlled aliphatic C-H oxidations with a predictive model for site-selectivity.

Paul E Gormisky1, M Christina White

  • 1Department of Chemistry, University of Illinois Urbana-Champaign , Urbana, Illinois 61801, United States.

Journal of the American Chemical Society
|September 12, 2013
PubMed
Summary

This study introduces a novel non-heme iron catalyst for selective aliphatic C-H bond oxidation. The catalyst demonstrates predictable control over site-selectivity across diverse organic molecules, offering broad synthetic applications.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Aliphatic C-H bonds are ubiquitous in organic molecules, making their selective oxidation a key challenge in synthesis.
  • Existing catalysts often lack broad substrate scope or predictable control over oxidation site-selectivity.
  • Enzyme-like, predictable control over reactivity is highly desired for synthetic applications.

Purpose of the Study:

  • To develop a simple, small-molecule catalyst for selective aliphatic C-H bond oxidation.
  • To achieve predictable catalyst-controlled site-selectivity across a wide range of substrates.
  • To establish a model correlating substrate properties with catalyst-controlled selectivity.

Main Methods:

  • Development of a non-heme iron catalyst.
  • Testing the catalyst's performance on topologically diverse aliphatic substrates.
  • Quantitative analysis correlating substrate physical properties with observed site-selectivities.

Main Results:

  • A simple non-heme iron catalyst was successfully synthesized and characterized.
  • The catalyst demonstrated predictable site-selectivity in the oxidation of various aliphatic C-H bonds.
  • Preparative yields were achieved for a broad range of substrates.
  • A quantitative model was established to predict selectivity based on substrate properties.

Conclusions:

  • The developed non-heme iron catalyst offers a powerful tool for selective aliphatic C-H bond oxidation.
  • Catalyst-controlled predictability in site-selectivity was achieved, overcoming inherent substrate preferences.
  • This work advances the field of C-H activation and provides a foundation for designing future catalysts.