Lignin Nanosphere-Supported Cuprous Oxide as an Efficient Catalyst for Huisgen [3+2] Cycloadditions under Relatively Mild Conditions
Abstract
:1. Introduction
2. Materials and Methods
2.1. Electrospraying Lignin Nanopheres
2.2. Preparation of Cu2O@L
2.3. Catalytic Performance Test
2.4. Analyses
3. Results
3.1. Characterization of the Electrosprayed Lignin Nanosphere and Cu2O@L
3.2. Catalytic Performance of Lignin Nanosphere-Supported Catalyst in the Huisgen “Click” Reaction
4. Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Acknowledgments
Conflicts of Interest
Abbreviations
XRD | X-ray powder diffraction |
SEM | Scanning electron microscopy |
TEM | Transmission electron microscopy |
XPS | X-ray photoelectron spectroscopy |
AFM | Atomic force microscope |
LSCM | Laser scanning confocal microscope |
EDS | Energy dispersive analysis system of X-ray |
TGA | Thermogravimetric analysis |
FT-NMR | Fourier transform nuclear magnetic resonance |
UV–vis–NIR | UV-visible-near infrared spectroscopy |
FTIR | Flourier transformation infrared spectroscopy |
AAS | Atomic absorption spectrophotometry |
Cu2O@L | the lignin nanosphere-supported cuprous oxide |
DMF | N,N-dimethylformamide |
ID | inner diameter |
FL | Fluorescence spectra |
PMT | Photomultiplier tube |
MW | weight-average molecular weight |
TMS | tetramethylsilane |
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Reaction | Alkyl Halide | Alkyne | Product a,b | Yield (%) c |
---|---|---|---|---|
1 | | | | 99 |
2 | | | | 98 |
3 | | | | 98 |
4 | | | | 98 |
5 | | | | 99 |
6 | | | | 98 |
7 | | | | 97 |
8 | | | | 96 |
9 | | | | 99 |
10 | | | | 97 |
11 | | | | 98 |
12 | | | | 98 |
13 | | | | 99 |
14 | | | | 96 |
15 | | | | 98 |
16 | | | | 99 |
Entry | Catalyst | mol % a | Solvent | T (°C) | Time (h) | Yield (%) | Ref. |
---|---|---|---|---|---|---|---|
1 | Copper in charcoal | 5 | dioxane | 25 | 10 | 84 | [47] |
2 | Copper in zeolite | 10 | toluene | 25 | 15 | 94 | [48] |
3 | CuSO4·5H2O | 1 | H2O/t-BuOH | 90 | 8 | 89 | [49] |
4 | Photocatalytic-Cu(II) | 5 | ethanol | 25 | 5 | 96 | [50] |
5 | Dendrimer-CuI | 0.5 | H2O | 25 | 3 | 98 | [51] |
6 | Chitosan-CuSO4 | 0.4 | H2O | 25 | 4–6 | 99 | [8] |
7 | Cu on chelated resins | 1 | solvent-free | 50/80 | 24/4 | 100 | [52] |
8 | CuCl/microwaves | 2.5 | glycerol | 100 | 0.5 | 82 | [53] |
9 | CuOAc/ball-milling | 10 | solvent-free | - | 1 | 90 | [54] |
10 | CuO@Nb2O5/UV | 1–1.2 | THF | 25 | 6 | 99 | [55] |
11 | Cu2O Nanocrystals | 6.25 | EtOH | 55 | 1 | 96 | [56] |
12 | Cu2O@L | 1.2 | solvent-free | 25 | 3 | 99 | This work |
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Zhou, Z.; Peng, X.; Zhong, L.; Li, X.; Sun, R. Lignin Nanosphere-Supported Cuprous Oxide as an Efficient Catalyst for Huisgen [3+2] Cycloadditions under Relatively Mild Conditions. Polymers 2018, 10, 724. https://doi.org/10.3390/polym10070724
Zhou Z, Peng X, Zhong L, Li X, Sun R. Lignin Nanosphere-Supported Cuprous Oxide as an Efficient Catalyst for Huisgen [3+2] Cycloadditions under Relatively Mild Conditions. Polymers. 2018; 10(7):724. https://doi.org/10.3390/polym10070724
Chicago/Turabian StyleZhou, Zidan, Xinwen Peng, Linxin Zhong, Xuehui Li, and Runcang Sun. 2018. "Lignin Nanosphere-Supported Cuprous Oxide as an Efficient Catalyst for Huisgen [3+2] Cycloadditions under Relatively Mild Conditions" Polymers 10, no. 7: 724. https://doi.org/10.3390/polym10070724