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Updated: Dec 26, 2025

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

Conditional Copper-Catalyzed Azide-Alkyne Cycloaddition by Catalyst Encapsulation.

Tobias G Brevé¹, Mike Filius², Can Araman³

¹Department of Chemical Engineering, Delft University of Technology, van der Maasweg 9, 2629 HZ, Delft, The Netherlands.

Angewandte Chemie (International Ed. in English)

|March 18, 2020

Summary

This summary is machine-generated.

Supramolecular encapsulation with cucurbit[7]uril (CB[7]) temporarily inactivates copper catalysts. A chemical signal releases the catalyst, enabling on-demand copper-catalyzed alkyne-azide cycloaddition (CuAAC) reactions for small molecules and proteins.

Keywords:

catalysis click chemistry cucurbit[n]uril host-guest systems protein labeling

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Area of Science:

Supramolecular Chemistry
Catalysis
Chemical Biology

Background:

Supramolecular encapsulation alters guest molecule properties.
Controlling catalyst activity temporally is crucial for chemical reactions.
Copper(I)-carbene catalysts are widely used in click chemistry.

Purpose of the Study:

To temporally control the catalytic activity of a copper(I)-carbene catalyst using supramolecular encapsulation.
To demonstrate on-demand activation of copper-catalyzed alkyne-azide cycloaddition (CuAAC) reactions.
To apply this method for protein labeling.

Main Methods:

Encapsulation of a copper(I)-carbene catalyst within cucurbit[7]uril (CB[7]).
Inhibition and subsequent activation of the catalyst using a chemical signal.
Application of the controlled catalyst for protein labeling (vinculin).

Main Results:

Encapsulation by CB[7] completely inactivated the copper catalyst in CuAAC reactions.
Addition of a chemical signal led to near-instantaneous catalyst activation.
Successful protein labeling of vinculin was achieved using the on-demand catalytic system.

Conclusions:

Supramolecular encapsulation provides a method for temporal control of copper-catalyzed click chemistry.
This strategy allows for on-demand activation of catalysts for both small molecules and protein targets.
The developed system offers precise temporal control over catalytic processes.