Fe/ppm Cu nanoparticles as a recyclable catalyst for click reactions in water at room temperature

Fe/ppm Cu nanoparticles as a recyclable catalyst for click reactions in water at room temperature

Green Chem., 2017, 19,2506-2509
DOI: 10.1039/C7GC00883J, Communication

Aurelien Adenot, Evan B. Landstrom, Fabrice Gallou, Bruce H. Lipshutz
Nanomicelles housing a terminal alkyne and azide are delivered to ppm Cu-containing nanoparticles that catalyse click reactions in water at rt.

 

Fe/ppm Cu nanoparticles as a recyclable catalyst for click reactions in water at room temperature

Aurélien Adenot,a  Evan B. Landstrom,a  Fabrice Galloub  and  Bruce H. Lipshutz*a 

*Corresponding authors

aDepartment of Chemistry & Biochemistry, University of California, Santa Barbara, USA
E-mail: lipshutz@chem.ucsb.edu

bNovartis Pharma A6, Basel, Switzerland

Abstract

New iron-based nanoparticles doped with ppm levels of CuOAc are capable of catalyzing cycloadditions between alkynes and azides to afford triazole-containing products. These reactions take place in water at ambient temperatures, enabled by the presence of nanomicelles that function as a delivery mechanism. The NPs can be easily recycled within the same reaction vessel. Low levels of residual copper are found in the product.

(2) 1-Benzyl-4-phenyl-1H-1,2,3-triazole. Isolated as a white powdery crystal (99%).

Rf = 0.33 (1:3 EtOAc: hexanes).

NMR 1 H (CDCl3, 500 MHz, δ): 7.79-7.81 (m, 2H), 7.66 (s, 1H), 7.37-7.42 (m, 5H), 7.30-7.33 (m, 3H), 5.59 (s, 2H).

Melting point: 123-125 o C.

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