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

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.

Reactivity of Enols

Reactivity of Enols

Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is...

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.

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

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...

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...

You might also read

Related Articles

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

Sort by

Same author

Progress toward a Nonenzymatic Gluconeogenesis: One-Pot Reactions and Model Systems.

JACS Au·2026

Same author

Alkoxysulfonium Salts Unlock Access to New Aryl Sulfonium Salts for Cross-Coupling.

Angewandte Chemie (International ed. in English)·2026

Same author

Computational study of the effect of Lewis base additives and molecular spin state in SmI<sub>2</sub>-chemistry.

Chemical science·2026

Same author

Visible Light-Promoted Cascade Cyclization/Allylation of 2-Allyloxyaryl Sulfonium Salts with Morita-Baylis-Hillman Acetates.

Organic letters·2026

Same author

Switchable N-H <i>vs</i>. C3-H carboxylation of indoles using dual-function reagents.

Chemical communications (Cambridge, England)·2026

Same author

Aryl Halide Carboxylation via Decarboxylative Metal-Halogen Exchange.

JACS Au·2026

Search research articles

Related Experiment Video

Updated: Nov 2, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Copper-catalyzed functionalization of enynes.

Quentin Dherbassy¹, Srimanta Manna¹, Fabien J T Talbot¹

¹Department of Chemistry, University of Manchester Oxford Road Manchester M13 9PL UK david.j.procter@manchester.ac.uk www.twitter.com/GroupProcter https://www.proctergroupresearch.com/.

Chemical Science

|June 7, 2021

Summary

Copper catalysis enables versatile enyne functionalization, yielding complex molecules. This review covers key copper-catalyzed reactions like borylation, hydrofunctionalization, and cyclizations for enynes.

More Related Videos

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Related Experiment Videos

Last Updated: Nov 2, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Area of Science:

Organic Chemistry
Catalysis
Synthetic Chemistry

Background:

Enyne derivatives are versatile building blocks in organic synthesis.
Copper catalysis offers efficient methods for functionalizing enynes.
These reactions produce highly functionalized and enantioenriched products.

Purpose of the Study:

To review recent advances in copper-catalyzed enyne functionalization.
To highlight key transformations including boro-, hydro-, and difunctionalizations.
To discuss mechanistic insights, particularly for 1,3-enyne regiodivergent reactions.

Main Methods:

Review of literature on copper-catalyzed enyne reactions.
Focus on boro- and hydrofunctionalizations.
Analysis of copper-mediated radical difunctionalizations and cyclizations.

Main Results:

Copper catalysis provides diverse routes for enyne functionalization.
Regiodivergent functionalization of 1,3-enynes is a key area.
Mechanistic understanding of these transformations is advancing.

Conclusions:

Copper-catalyzed enyne functionalization is a powerful synthetic strategy.
The versatility of enynes allows access to complex molecular architectures.
Continued research promises further development in this field.