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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.

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.

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...

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...

¹H NMR: Long-Range Coupling

¹H NMR: Long-Range Coupling

The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...

You might also read

Related Articles

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

Sort by

Same author

Bulky Terphenyl Phosphines Stabilize Otherwise Highly Reactive Iridium Fragments, Key in C-H Activation Reactions.

Inorganic chemistry·2026

Same author

A photoexcited triplet state germylene with a half-life of hours at room temperature.

Nature chemistry·2026

Same author

Experimental and theoretical studies on the (co)cyclotrimerization of alkynes (and ethylene) in a TpRh compound.

Dalton transactions (Cambridge, England : 2003)·2026

Same author

Metal-metal <i>vs.</i> metal-ligand cooperation in iron-mediated activation and catalytic reduction of nitrous oxide and nitrobenzene.

Chemical science·2026

Same author

Synthesis and Characterization of a Copper Complex Supported by a Z‑type Sb<sup>V</sup> Ligand: XPS and DFT Study of Electronic Structure.

Organometallics·2026

Same author

Rhodium-Catalyzed Arene Alkenylation Using Benzoquinone Derivatives as Oxidants.

Organometallics·2026

Search research articles

Related Experiment Video

Updated: Nov 18, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Reductive C-C Coupling from Molecular Au(I) Hydrocarbyl Complexes: A Mechanistic Study.

Juan Miranda-Pizarro¹, Zhongwen Luo², Juan J Moreno¹

¹Instituto de Investigaciones Químicas (IIQ), Departamento de Química Inorgánica and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Sevilla and Consejo Superior de Investigaciones Científicas (CSIC), Avenida Américo Vespucio 49, 41092 Sevilla, Spain.

Journal of the American Chemical Society

|February 5, 2021

Summary

This study explores organometallic gold complexes for C-C coupling, forming ethane from gem-digold methyl complexes. Reaction rates depend on phosphine substituents and show second-order kinetics, suggesting a multi-step mechanism.

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: Nov 18, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 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:

Organometallic Chemistry
Catalysis
Gold Complexes

Background:

Organometallic gold complexes are vital precursors in catalytic reactions, particularly for carbon-carbon bond formation.
Understanding the mechanisms of these reactions is crucial for designing more efficient catalytic systems.

Purpose of the Study:

To investigate the C-C coupling reaction forming ethane from various phosphine-ligated gem-digold(I) methyl complexes.
To elucidate the reaction mechanism, including the role of phosphine ligands and steric effects.

Main Methods:

Synthesis of gem-digold methyl complexes via reaction of Au(CH3)L and Au(L)(NTf2).
Solid-state X-ray structure determination for key complexes.
Kinetic studies using multinuclear NMR spectroscopy to monitor ethane elimination rates.
Computational methods to support mechanistic proposals.

Main Results:

Ethane formation rate from [Au2(μ-CH3)(PMe2Ar')2][NTf2] is inversely related to the steric bulk of the Ar' phosphine substituent.
Ethane elimination reactions exhibit a second-order dependence on the gem-digold methyl complexes.
Solid-state X-ray structures were obtained for complexes with XPhos and tBuXPhos ligands.

Conclusions:

A detailed mechanism for C-C coupling is proposed, involving complex dissociation, phosphine migration, and recombination.
The Lewis acidity of gold fragments and steric properties of phosphine ligands significantly influence the reaction pathway and rate.
This research provides fundamental insights into the reactivity of digold complexes in C-C bond formation.