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Peptide Conjugation via CuAAC ‘Click’ Chemistry
Article

Solvent-Free Copper-Catalyzed Azide-Alkyne Cycloaddition under Mechanochemical Activation

1
Dipartimento di Scienza e Tecnologia del Farmaco and NIS—Centre for Nanostructured Interfaces and Surfaces, University of Turin, Via P. Giuria 9, Turin 10125, Italy
2
Dipartimento di Biotecnologie Molecolari e Scienze per la Salute, University of Turin, Via Quarello 15, Turin 10125, Italy
*
Author to whom correspondence should be addressed.
Academic Editor: Arnaud Gautier
Molecules 2015, 20(2), 2837-2849; https://doi.org/10.3390/molecules20022837
Received: 6 January 2015 / Accepted: 2 February 2015 / Published: 9 February 2015
(This article belongs to the Collection Advances in Click Chemistry)
The ball-mill-based mechanochemical activation of metallic copper powder facilitates solvent-free alkyne-azide click reactions (CuAAC). All parameters that affect reaction rate (i.e., milling time, revolutions/min, size and milling ball number) have been optimized. This new, efficient, facile and eco-friendly procedure has been tested on a number of different substrates and in all cases afforded the corresponding 1,4-disubstituted 1,2,3-triazole derivatives in high yields and purities. The final compounds were isolated in almost quantitative overall yields after simple filtration, making this procedure facile and rapid. The optimized CuAAC protocol was efficiently applied even with bulky functionalized β-cyclodextrins (β-CD) and scaled-up to 10 g of isolated product. View Full-Text
Keywords: click reaction; copper catalyzed alkyne-azide cycloaddition; ball mill; solvent-free reaction; mechanochemistry click reaction; copper catalyzed alkyne-azide cycloaddition; ball mill; solvent-free reaction; mechanochemistry
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MDPI and ACS Style

Rinaldi, L.; Martina, K.; Baricco, F.; Rotolo, L.; Cravotto, G. Solvent-Free Copper-Catalyzed Azide-Alkyne Cycloaddition under Mechanochemical Activation. Molecules 2015, 20, 2837-2849. https://doi.org/10.3390/molecules20022837

AMA Style

Rinaldi L, Martina K, Baricco F, Rotolo L, Cravotto G. Solvent-Free Copper-Catalyzed Azide-Alkyne Cycloaddition under Mechanochemical Activation. Molecules. 2015; 20(2):2837-2849. https://doi.org/10.3390/molecules20022837

Chicago/Turabian Style

Rinaldi, Laura, Katia Martina, Francesca Baricco, Laura Rotolo, and Giancarlo Cravotto. 2015. "Solvent-Free Copper-Catalyzed Azide-Alkyne Cycloaddition under Mechanochemical Activation" Molecules 20, no. 2: 2837-2849. https://doi.org/10.3390/molecules20022837

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