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Molecules. 2015 Feb 9;20(2):2837-49. doi: 10.3390/molecules20022837.

Solvent-free copper-catalyzed azide-alkyne cycloaddition under mechanochemical activation.

Author information

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. laura.rinaldi@unito.it.
2
Dipartimento di Biotecnologie Molecolari e Scienze per la Salute, University of Turin, Via Quarello 15, Turin 10125, Italy. laura.rinaldi@unito.it.
3
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. katia.martina@unito.it.
4
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. francesca.baricco@hotmail.it.
5
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. giancarlo.cravotto@unito.it.

Abstract

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.

PMID:
25671367
DOI:
10.3390/molecules20022837
[Indexed for MEDLINE]
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