Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

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.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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...
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

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

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, dissociates into a...
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...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Evaluation of the RTyper Y27 chip amplification system with Quick TargSeq 1.0 for Y-STR genotyping in forensic science.

International journal of legal medicine·2026
Same author

SNORA11B recruits SWI/SNF to suppress esophageal squamous cell carcinoma malignancy by promoting GPD1-mediated G3P accumulation and mitochondrial damage.

Oncogene·2026
Same author

The role of mitochondria in the gut-kidney axis: implications for kidney health.

Frontiers in pharmacology·2026
Same author

Cobalt/Photoredox Dual-Catalyzed Alkylation of Indole with Unactivated Alkenes.

Organic letters·2026
Same author

Crosstalk in the kidney-muscle axis: myokines and muscle-relevant mediators in chronic kidney disease-associated sarcopenia.

Frontiers in medicine·2026
Same author

CPSF2-mediated 3' UTR truncation of MTERF3 drives mitochondrial dysfunction and osteosarcoma progression.

Oncogene·2026

Related Experiment Video

Updated: May 12, 2026

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

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

Published on: May 21, 2019

How Silver Additives Promote Copper-Catalyzed Cyclization and Alkene Transposition: A Mechanistic Study.

Lan Hu1, Lihan Zhu1, Guangfan Zheng1

  • 1Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, North-east Normal University, Changchun 130024, China.

Organic Letters
|May 11, 2026
PubMed
Summary

Silver additives stabilize copper-catalyzed spirocyclic ether synthesis by forming a synergistic catalytic framework. This framework enhances key hydrogen transfer processes through intricate metal-ligand interactions, revealing a bimetallic effect.

More Related Videos

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Related Experiment Videos

Last Updated: May 12, 2026

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

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

Published on: May 21, 2019

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Computational Chemistry

Background:

  • Copper-catalyzed reactions are vital for synthesizing complex organic molecules.
  • Alkenol transposition/cyclization efficiently forms spirocyclic ethers.
  • The role of silver (Ag) additives in these copper (Cu)-catalyzed reactions is not well understood.

Purpose of the Study:

  • To elucidate the precise function of silver additives in copper-catalyzed alkene transposition/cyclization of alkenols.
  • To provide a detailed mechanistic understanding of the observed bimetallic effect.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed to model the catalytic system.
  • Quantum Theory of Atoms in Molecules (QTAIM) analyses were used to investigate electronic interactions.
  • Energy Decomposition Analysis (EDA) was performed to quantify interaction energies.

Main Results:

  • Silver (Ag) forms a stable, multidentate coordination framework that promotes synergistic catalysis with copper (Cu).
  • Ag···C, Ag···O, Ag···H, and Ag···Cu interactions are crucial for stabilizing the hydrogen transfer step.
  • EDA revealed that orbital, electrostatic, and dispersion interactions synergistically contribute to stabilization.

Conclusions:

  • Silver additives play a critical role in enhancing copper-catalyzed spirocyclic ether formation through a synergistic bimetallic effect.
  • The study provides a quantitative mechanistic rationale for silver's function, based on detailed electronic structure analyses.