Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

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

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

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.

Olefin Metathesis Polymerization: Overview

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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.

Oxymercuration-Reduction of Alkenes

Oxymercuration-Reduction of Alkenes

Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.

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

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

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.’

Reduction of Alkenes: Catalytic Hydrogenation

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...

You might also read

Related Articles

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

Sort by

Same author

C-glycoside synthesis via radical cross-coupling of glycohydrazides.

Nature·2026

Same author

Stereoretentive radical-based alkyl-alkyl cross-coupling.

Science (New York, N.Y.)·2026

Same author

Electronegatively substituted adamantyl units accelerate chemiexcitation of 1,2-dioxetane luminophores while preserving chemical stability.

Chemical science·2026

Same author

Enabling Access to sp<sup>3</sup>-Enriched Targeted Protein Degraders via Redox-Neutral Radical Cross-Coupling.

Angewandte Chemie (International ed. in English)·2026

Same author

Arylhydrazines: Convenient Homogeneous Reductants for Scalable Cross-Coupling.

Angewandte Chemie (International ed. in English)·2026

Same author

Decoding the Nested, Multicycle Mechanism of Ni-Catalyzed Redox-Neutral Cross-Coupling through Temperature Scanning Reaction Calorimetry.

Journal of the American Chemical Society·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

Search research articles

Related Experiment Video

Updated: May 4, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

A practical and catalytic reductive olefin coupling.

Julian C Lo¹, Yuki Yabe, Phil S Baran

¹Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society

|January 17, 2014

Summary

This summary is machine-generated.

Researchers developed a cost-effective iron-catalyzed method for directly coupling olefins. This reaction efficiently creates complex molecules, including hindered bicyclic systems and quaternary centers, offering a new synthetic pathway.

More Related Videos

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Related Experiment Videos

Last Updated: May 4, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Direct olefin coupling is a crucial transformation in organic synthesis.
Existing methods often require expensive catalysts or harsh conditions.
Accessing complex structures like vicinal quaternary centers remains challenging.

Purpose of the Study:

To develop a redox-economic and cost-effective method for direct olefin coupling.
To enable the synthesis of challenging molecular architectures using readily available starting materials.
To provide a robust and scalable synthetic route for complex organic compounds.

Main Methods:

Utilized an inexpensive iron catalyst for the direct coupling of olefins.
Employed a silane reducing agent to facilitate the redox process.
Investigated both intramolecular and intermolecular coupling reactions.

Main Results:

Successfully coupled unactivated olefins with electron-deficient olefins.
Generated hindered bicyclic systems, vicinal quaternary centers, and cyclopropanes in good yields.
Demonstrated robustness to oxygen and moisture, with successful gram-scale synthesis.

Conclusions:

The reported iron-catalyzed method offers a novel and efficient approach to direct olefin coupling.
This strategy provides access to valuable compounds previously difficult to synthesize.
The reaction's practicality and scalability make it a significant advancement in synthetic organic chemistry.