Related Experiment Video
Updated: Dec 24, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Versatile strained alkyne modified water-soluble AuNPs for interfacial strain promoted azide-alkyne cycloaddition
Pierangelo Gobbo1, Zack Mossman, Ali Nazemi
1The University of Western Ontario and the Centre for Materials and Biomaterials Research, Richmond Street, London, Ontario, Canada. mworkent@uwo.ca.
Abstract:
Versatile water- and organic solvent-soluble AuNPs that incorporate an interfacial strained alkyne capable of efficient pour and mix strain promoted interfacial cycloadditions with azide partners have been synthesized and carefully characterized for the first time. The use of XPS to quantitate the loading of the strained alkyne on the AuNPs is noteworthy. The reactivity towards the interfacial strain promoted azide-alkyne cycloaddition reaction was demonstrated by using azide-decorated polymersomes as bioorthogonal reaction partners.
Related Concept Videos
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

