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. 2019 Feb 19:7:81.
doi: 10.3389/fchem.2019.00081. eCollection 2019.

Sustainable Construction of Heterocyclic 1,2,3-Triazoles by Strict Click [3+2] Cycloaddition Reactions Between Azides and Alkynes on Copper/Carbon in Water

Noura Aflak  1 , Hicham Ben El Ayouchia  1 , Lahoucine Bahsis  1 , El Mountassir El Mouchtari  1 , Miguel Julve  2 , Salah Rafqah  1 , Hafid Anane  1 , Salah-Eddine Stiriba  1   2
Affiliations

Sustainable Construction of Heterocyclic 1,2,3-Triazoles by Strict Click [3+2] Cycloaddition Reactions Between Azides and Alkynes on Copper/Carbon in Water

Noura Aflak et al. Front Chem. .

Abstract

1,4-Disubstituted-1,2,3-triazoles, considered as an important and useful class of heterocycles with potential applications in material science and biology, have been prepared in an efficient and selective manner by copper on carbon-catalyzed [3+2] cycloaddition reactions of azides and alkynes (CuAAC) in water under strict click chemistry conditions. Copper(I) catalysts heterogenized onto commercially activated carbon materials (Cu-CC) and on another carbon material produced from vegetable biomass using Argan nut shells (Cu-CANS) were found to be versatile catalytic sources for sustainable CuAAC. These copper on carbon supports were prepared and fully characterized by using two types of activated carbons that exhibit different porosity and specific surface. The delineation of the nature of the catalytic copper species and the role of the carbon support in the CuAAC were addressed. These heterogeneous copper on carbon catalysts were recovered and reused until ten catalytic runs without any noticeable loss of activity.

Keywords: 1, 2, 3-triazole; activated carbon; click chemistry; copper; heterogeneous catalyst; recovery/recycling; water.

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Figures

Scheme 1
Scheme 1
Lipshutz's protocol for the preparation of “copper-in-charcoal.”
Scheme 2
Scheme 2
Preparation scheme of copper on carbon support made from Argan nut shells Cu-CANS.
Figure 1
Figure 1
XRD results of CANS support (A), Cu-CANS material (B), and phenylacetylene in Cu-CANS (C).
Figure 2
Figure 2
XRD results of CC support (A), Cu-CC material (B), and phenylacetylene in Cu-CC (C).
Figure 3
Figure 3
Comparative FT-IR spectra of CuI precursor (red), Cu-CC (blue), and Cu-CANS material (green).
Figure 4
Figure 4
SEM images of CANS support (a), Cu-CANS (b), and Cu-CC material (c).
Figure 5
Figure 5
EDX spectrum of (A) CANS and (B) Cu-CANS catalyst.
Figure 6
Figure 6
The proposed mechanism for the formation of 1-4-disubstituted-1,2,3-triazoles catalyzed by Cu/carbon.
Figure 7
Figure 7
Recycling results of the Cu-CC and Cu-CANS catalytic systems in the copper-catalyzed cycloaddition reaction of phenylacetylene and benzyl azide.
See this image and copyright information in PMC

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