Green Methodologies for Copper(I)-Catalyzed Azide-Alkyne Cycloadditions: A Comparative Study

Marissa Trujillo; Clayton Hull-Crew; Andrew Outlaw; Kevin Stewart; Loren Taylor; Laura George; Allison Duensing; Breanna Tracey; Allen Schoffstall

doi:10.3390/molecules24050973

Molecules (Mar 2019)

Green Methodologies for Copper(I)-Catalyzed Azide-Alkyne Cycloadditions: A Comparative Study

Marissa Trujillo,
Clayton Hull-Crew,
Andrew Outlaw,
Kevin Stewart,
Loren Taylor,
Laura George,
Allison Duensing,
Breanna Tracey,
Allen Schoffstall

Affiliations

Marissa Trujillo: Department of Chemistry and Biochemistry, University of Colorado Colorado Springs, Colorado Springs, CO 80918, USA
Clayton Hull-Crew: Department of Chemistry and Biochemistry, University of Colorado Colorado Springs, Colorado Springs, CO 80918, USA
Andrew Outlaw: Department of Chemistry and Biochemistry, University of Colorado Colorado Springs, Colorado Springs, CO 80918, USA
Kevin Stewart: Department of Chemistry and Biochemistry, University of Colorado Colorado Springs, Colorado Springs, CO 80918, USA
Loren Taylor: Department of Chemistry and Biochemistry, University of Colorado Colorado Springs, Colorado Springs, CO 80918, USA
Laura George: Department of Chemistry and Biochemistry, University of Colorado Colorado Springs, Colorado Springs, CO 80918, USA
Allison Duensing: Department of Chemistry and Biochemistry, University of Colorado Colorado Springs, Colorado Springs, CO 80918, USA
Breanna Tracey: Department of Chemistry and Biochemistry, University of Colorado Colorado Springs, Colorado Springs, CO 80918, USA
Allen Schoffstall: Department of Chemistry and Biochemistry, University of Colorado Colorado Springs, Colorado Springs, CO 80918, USA

DOI: https://doi.org/10.3390/molecules24050973
Journal volume & issue: Vol. 24, no. 5
p. 973

Abstract

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Successful copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions may be achieved by several methods. In this paper, four synthetic protocols were performed for direct comparison of time required for the synthesis, yield, and purity of the 1H-1,2,3-triazole products. The methods with Cu(I) catalysts were conventional, microwave heating, solvent-free, and a method using glycerol solvent. The compounds synthesized in this paper were known non-fluorinated triazoles and new fluorinated triazoles. The results lead to the conclusion that the microwave method should be strongly considered for CuAAC syntheses.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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