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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.9K
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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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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Free-Radical Chain Reaction and Polymerization of Alkenes02:35

Free-Radical Chain Reaction and Polymerization of Alkenes

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The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
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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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Radical Anti-Markovnikov Addition to Alkenes: Thermodynamics01:32

Radical Anti-Markovnikov Addition to Alkenes: Thermodynamics

2.7K
The anti-Markovnikov addition of hydrogen halides to an alkene is thermodynamically feasible only with HBr. The radical addition reaction with other hydrogen halides like HCl and HI is thermodynamically unfavorable.
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Updated: Feb 6, 2026

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

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Catalytic Alkene Difunctionalization via Imidate Radicals.

Kohki M Nakafuku1, Stacy C Fosu1, David A Nagib1

  • 1Department of Chemistry and Biochemistry , The Ohio State University , Columbus , Ohio 43210 , United States.

Journal of the American Chemical Society
|August 30, 2018
PubMed
Summary

Researchers developed a new catalytic method using imidate radicals for alkene difunctionalization. This photocatalytic approach enables hydroamination, aminoalkylation, and aminoarylation of allyl alcohols with broad utility.

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Radical Chemistry

Background:

  • Imidate radicals are versatile intermediates in organic synthesis.
  • Developing catalytic methods for generating and utilizing N-centered radicals is crucial for new reaction pathways.

Purpose of the Study:

  • To establish the first catalytic strategy for harnessing imidate radicals.
  • To enable alkene difunctionalization of allyl alcohols via photocatalytic reduction of oxime imidates.

Main Methods:

  • Photocatalytic reduction of oxime imidates to generate imidate radicals.
  • Exploration of consecutive intra- and intermolecular radical reactions.
  • Investigation of three distinct radical mechanisms: hydroamination, aminoalkylation, and aminoarylation.

Main Results:

  • Successful development of a catalytic strategy for imidate radical generation and reactivity.
  • Demonstration of alkene difunctionalization of allyl alcohols.
  • Achieved hydroamination, aminoalkylation, and aminoarylation products through distinct radical pathways.

Conclusions:

  • This work presents a novel and broadly applicable catalytic method for imidate radical chemistry.
  • The developed approach expands the toolkit for N-centered radical reactions and offers complementary pathways to existing methods.