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

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

2.2K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
2.2K
Electrophiles02:28

Electrophiles

12.6K
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
12.6K
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.
2.3K
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

3.3K
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
3.3K
Oxidation-Reduction Reactions03:11

Oxidation-Reduction Reactions

75.2K
Oxidation–Reduction Reactions
75.2K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.4K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
2.4K

You might also read

Related Articles

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

Sort by
Same author

[Renal sodium transporters in salt-sensitive hypertension].

Sheng li xue bao : [Acta physiologica Sinica]·2026
Same author

Deoxygenative phosphonation of ketones by titanium.

Chemical science·2026
Same author

Fu Zheng Li Qi Tang combined with FOCUS-PDCA model in postoperative rehabilitation of elderly biliary surgery patients.

World journal of gastrointestinal surgery·2026
Same author

Nickel-Catalyzed Enantioconvergent Cross-Electrophile Coupling of Benzylic Alcohols with Alkenyl Electrophiles.

Journal of the American Chemical Society·2025
Same author

Direct Deoxygenative Formylation of Ketones with Titanium.

Organic letters·2025
Same author

Alginate oligosaccharide prevents renal ischemia-reperfusion injury in rats via MRC1-mediated pathway.

Acta pharmacologica Sinica·2025
Same journal

A Ni-Mediated Cross-Coupling Approach to Deuterated <sup>18</sup>F- Fluoromethylated (Hetero)arenes.

Journal of the American Chemical Society·2026
Same journal

Efficient Light-Driven CO<sub>2</sub> Capture and Reversible Release Enabled by Metastable Photoacid-Decorated Metal-Organic Frameworks.

Journal of the American Chemical Society·2026
Same journal

In Situ Raman Spectroscopy Reveals the Dynamic Evolution and Ethanol Dependence of SEI Structure in Li-Mediated N<sub>2</sub> Reduction Reaction.

Journal of the American Chemical Society·2026
Same journal

Solvent Esterification and Stoichiometric Control in Ambient-Grown FAPbI<sub>3</sub> Single-Crystal Solar Cells.

Journal of the American Chemical Society·2026
Same journal

Unlocking Azulene Functionalization via Strain-Induced Azulyne Intermediates.

Journal of the American Chemical Society·2026
Same journal

An Oxazine-Locked Covalent Organic Framework by a Tandem Pinner/Schiff Base Reaction for Hydrogen Peroxide Photosynthesis.

Journal of the American Chemical Society·2026
See all related articles

Related Experiment Video

Updated: Jan 21, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.4K

Reductive Coupling between C-N and C-O Electrophiles.

Rong-De He1, Chun-Ling Li1, Qiu-Quan Pan1

  • 1State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering , Lanzhou University , 222 South Tianshui Road , Lanzhou 730000 , China.

Journal of the American Chemical Society
|August 1, 2019
PubMed
Summary
This summary is machine-generated.

This study introduces a novel cross-electrophile coupling reaction, forming carbon-carbon bonds by cleaving carbon-nitrogen and carbon-oxygen bonds. This expands C-C bond formation strategies beyond traditional organic halides.

More Related Videos

Growing Protein Crystals with Distinct Dimensions Using Automated Crystallization Coupled with In Situ Dynamic Light Scattering
09:15

Growing Protein Crystals with Distinct Dimensions Using Automated Crystallization Coupled with In Situ Dynamic Light Scattering

Published on: August 14, 2018

11.0K
Monitoring On-Target Signaling Responses in Larval Zebrafish - Z-REX Unmasks Precise Mechanisms of Electrophilic Drugs and Metabolites
05:28

Monitoring On-Target Signaling Responses in Larval Zebrafish - Z-REX Unmasks Precise Mechanisms of Electrophilic Drugs and Metabolites

Published on: June 2, 2023

1.4K

Related Experiment Videos

Last Updated: Jan 21, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.4K
Growing Protein Crystals with Distinct Dimensions Using Automated Crystallization Coupled with In Situ Dynamic Light Scattering
09:15

Growing Protein Crystals with Distinct Dimensions Using Automated Crystallization Coupled with In Situ Dynamic Light Scattering

Published on: August 14, 2018

11.0K
Monitoring On-Target Signaling Responses in Larval Zebrafish - Z-REX Unmasks Precise Mechanisms of Electrophilic Drugs and Metabolites
05:28

Monitoring On-Target Signaling Responses in Larval Zebrafish - Z-REX Unmasks Precise Mechanisms of Electrophilic Drugs and Metabolites

Published on: June 2, 2023

1.4K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Cross-electrophile reactions are key for C-C bond formation.
  • Existing research primarily utilizes organic halides as electrophiles.

Purpose of the Study:

  • To explore C-C bond formation using C-N and C-O electrophiles.
  • To demonstrate the cleavage of C-N and C-O bonds in coupling reactions.

Main Methods:

  • Investigated coupling reactions between benzyl/aryl ammonium salts (C-N electrophiles) and vinyl/aryl C-O electrophiles.
  • Conducted preliminary mechanistic studies.

Main Results:

  • Successfully achieved C-C bond formation via C-N and C-O bond cleavage.
  • Identified a radical mechanism for the activation of benzyl ammoniums.

Conclusions:

  • The study expands the scope of cross-electrophile reactions.
  • C-N and C-O electrophiles can be effectively used for C-C bond construction.