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Related Concept Videos

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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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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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.
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Catalysis02:50

Catalysis

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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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Reduction of Alkenes: Catalytic Hydrogenation02:13

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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.
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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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.
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Related Experiment Video

Updated: Jun 17, 2025

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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Ligand Oxidation Activates a Ruthenium(II) Precatalyst for C-H Hydroxylation.

Paul J Lauridsen1, Yeon Jung Kim1, Daniel P Marron1

  • 1Department of Chemistry, Stanford University, 337 Campus Drive, Stanford, California 94305, United States.

Journal of the American Chemical Society
|August 12, 2024
PubMed
Summary
This summary is machine-generated.

Researchers developed novel Ruthenium-sulfonamidate precatalysts for sp3 C-H hydroxylation. The optimal precatalyst, 2h, demonstrates high efficiency in aqueous conditions, challenging prior assumptions about ligand oxidation in catalysis.

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Last Updated: Jun 17, 2025

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Developing efficient catalysts for sp3 C-H hydroxylation is crucial for organic synthesis.
  • Ruthenium (Ru) complexes are widely explored for catalytic applications.
  • Understanding the role of ligand structure in catalyst performance is essential.

Purpose of the Study:

  • To introduce a new class of Ru-sulfonamidate precatalysts for sp3 C-H hydroxylation.
  • To identify an optimal precatalyst through structure-performance studies.
  • To elucidate the mechanism of catalysis, particularly the role of ligand oxidation.

Main Methods:

  • Synthesis of heteroleptic Ru(II) complexes.
  • Structure determination using single-crystal X-ray analysis.
  • Catalytic hydroxylation reactions in aqueous, biphasic solvent mixtures.
  • Comparative mechanistic studies involving kinetics, mass spectrometry, and electrochemistry.

Main Results:

  • An optimal precatalyst, 2h (Ru-sulfonamidate with dtbpy and pyridylsulfonamidate ligands), was identified.
  • Catalytic hydroxylation achieved yields of 37-90% using 1 mol% 2h and ceric ammonium nitrate.
  • Mechanistic studies revealed long-lived active species generated by 2h, leading to high turnover numbers.
  • Ligand oxidation was found to be a prerequisite for catalyst activation, contrary to previous findings.

Conclusions:

  • The novel Ru-sulfonamidate precatalysts offer a versatile and efficient route for sp3 C-H hydroxylation.
  • The optimal precatalyst 2h exhibits high activity and stability in aqueous media.
  • The findings challenge the conventional understanding of ligand oxidation in Ru-catalyzed reactions, opening new avenues for catalyst design.