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Related Concept Videos

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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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 trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

10.5K
Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal, such as sodium,...
10.5K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

13.9K
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...
13.9K
Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

12.1K
Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
12.1K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.3K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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One-Electron Approach for Trans-Selective Alkyne Semi-Reduction via Cobalt Catalysis.

Rakesh Mondal1, Lior Galmidi1, Avra Tzaguy1

  • 1Department of Molecular Chemistry and Materials Science, Weizmann Institute of Science, Rehovot 7610001, Israel.

Journal of the American Chemical Society
|October 28, 2025
PubMed
Summary
This summary is machine-generated.

This study presents a new cobalt-catalyzed electrochemical method for the selective trans-semireduction of internal alkynes to E-alkenes. This versatile approach offers broad substrate scope and functional group tolerance, advancing synthetic chemistry.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Electrochemistry

Background:

  • Diastereoselective semireduction of alkynes to alkenes is crucial in synthesis.
  • Existing catalytic methods for trans-selective (E) alkyne reduction are limited.
  • Developing new catalytic systems for selective alkyne transformations is essential.

Purpose of the Study:

  • To introduce a novel catalytic method for the highly selective trans-semireduction of internal alkynes.
  • To explore a cobalt-catalyzed electrochemical radical pathway for alkyne reduction.
  • To develop a general strategy for accessing E-alkenes from alkynes.

Main Methods:

  • Cobalt-catalyzed electrochemical radical pathway.
  • Cyclic voltammetry, UV-vis spectroelectrochemistry, and DFT calculations for mechanistic studies.
  • Development of a complementary chemical oxidative protocol.

Main Results:

  • Achieved highly selective trans-semireduction of internal alkynes to E-alkenes.
  • Demonstrated broad substrate scope, exceptional chemoselectivity, and functional group tolerance.
  • Established a dual catalytic cycle involving electrochemical Co-H formation and an organometallic radical pathway.

Conclusions:

  • Introduced a fundamentally new and general strategy for accessing trans-alkenes from alkynes via cobalt catalysis.
  • Opened a new avenue for radical-based alkyne functionalization.
  • Provided a complementary oxidative protocol for challenging substrates.