Related Experiment Video
Updated: Jun 8, 2025

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Capsules for Automated Azide-Alkyne Click Reactions.
Anna Konopka1, Guillaume Coin1, Paula L Nichols1
1Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zürich, Switzerland.
An automated process using prepacked capsules enables reproducible copper-mediated click reactions for synthesizing 1,2,3-triazoles. This fully automated method yields high-purity products without user intervention, streamlining organic synthesis.
Area of Science:
- Organic Chemistry
- Chemical Engineering
- Materials Science
Background:
- Copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a vital reaction in chemistry.
- Traditional CuAAC synthesis requires manual handling of reagents and purification steps.
- Reproducibility and automation are key challenges in synthetic organic chemistry.
Purpose of the Study:
- To develop an automated and reproducible method for copper-mediated click reactions.
- To utilize prepacked capsules for a fully automated synthesis and purification process.
- To demonstrate the efficiency of capsule-based automated organic synthesis for triazole production.
Main Methods:
- Development of prepacked capsules containing all reagents and materials for CuAAC reactions.
- Full automation of the reaction and product isolation steps.
- Sequential automated synthesis of organic azides followed by CuAAC in a second capsule.
Main Results:
- Successful synthesis of 1,4-disubstituted 1,2,3-triazole products with high purity.
- Demonstration of a fully automated process with no user involvement required.
- Proof-of-concept for sequential automated synthesis and click reactions without intermediate purification.
Conclusions:
- Capsule-based automated organic synthesis offers a reproducible and efficient approach for CuAAC reactions.
- The developed method significantly simplifies the synthesis of 1,2,3-triazoles.
- This automation strategy has broad implications for streamlining synthetic workflows in chemistry.
Related Concept Videos
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...
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

