Related Experiment Video
Updated: Oct 25, 2025

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
By-design molecular architectures via alkyne metathesis
Shaofeng Huang1, Zepeng Lei1, Yinghua Jin1
1Department of Chemistry, University of Colorado Boulder 80309 USA wei.zhang@colorado.edu.
Shape-persistent organic molecules are built using Dynamic Covalent Chemistry (DCvC). Ethynylene linkages formed via alkyne metathesis enable the creation of stable macrocycles and molecular cages with diverse applications.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
- Materials Science
Background:
- Shape-persistent purely organic molecular architectures are of significant research interest.
- Dynamic Covalent Chemistry (DCvC) provides efficient synthetic routes for constructing these architectures.
- Ethynylene linkages, formed via alkyne metathesis, offer desirable stability, linearity, and rigidity.
Purpose of the Study:
- To review synthetic strategies for discrete molecular architectures containing ethynylene linkages.
- To highlight the role of alkyne metathesis as a key synthetic step.
- To discuss the applications of these ethynylene-containing architectures.
Main Methods:
- Focus on alkyne metathesis for the formation of ethynylene linkages.
- Review of synthetic strategies for macrocycles and molecular cages.
- Discussion of catalyst development for alkyne metathesis.
Main Results:
- Exploration of historical challenges and advancements in alkyne metathesis.
- Presentation of novel macrocycle and molecular cage structures.
- Summary of the diverse applications of these molecular architectures.
Conclusions:
- Alkyne metathesis is a powerful tool for synthesizing shape-persistent organic architectures.
- Ethynylene linkages contribute to the stability and functionality of macrocycles and cages.
- Future outlook and remaining challenges in the field are discussed.
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.
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Olefin Metathesis Polymerization: Overview
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
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.
Acidity of 1-Alkynes
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.

