Related Experiment Video
Updated: Aug 10, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Acetylenic Coupling: A Powerful Tool in Molecular Construction
Siemsen1, Livingston, Diederich
1Laboratorium für Organische Chemie ETH-Zentrum Universitätstrasse 16, 8092 Zürich (Switzerland).
Acetylenic coupling methods are advancing, particularly palladium-catalyzed reactions, for synthesizing complex molecules. This review covers new techniques and mechanistic insights for acetylenic compounds.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Acetylenic coupling is crucial for natural products and molecular recognition.
- Pi-conjugated systems with acetylenic moieties exhibit unique electronic and optical properties.
Purpose of the Study:
- To comprehensively review acetylenic coupling protocols.
- To discuss recent advancements in mechanistic understanding and synthetic applications.
Main Methods:
- Review of classical Glaser conditions for homocoupling.
- Analysis of modern palladium-catalyzed methods for selective heterocoupling.
- Examination of synthetic challenges and new method development.
Main Results:
- Palladium-catalyzed couplings enhance selectivity and reliability in acetylenic reactions.
- New methods facilitate synthesis of complex macromolecular structures.
- Improved mechanistic understanding aids in developing advanced synthetic strategies.
Conclusions:
- Acetylenic coupling is a dynamic field with significant recent progress.
- Advanced coupling methods are essential for complex molecular synthesis.
- This review provides a unified perspective on acetylenic coupling methodologies.
Related Concept Videos
Preparation of Alkynes: Alkylation Reaction
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.
Cycloaddition Reactions: Overview
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
¹H NMR: 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 π orbitals.

