Highly active cellulose-supported poly(hydroxamic acid)-cu(II) complex for ullmann etherification
Highly active natural pandanus-extracted cellulose-supported poly(hydroxamic acid)−Cu(II) complex 4 was synthesized. The surface of pandanus cellulose was modified through graft copolymerization using purified methyl acrylate as a monomer. Then, copolymer methyl acrylate was converted into a bidenta...
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| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English English |
| Published: |
American Chemical Society
2021
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| Subjects: | |
| Online Access: | https://eprints.ums.edu.my/id/eprint/27248/1/Highly%20active%20cellulose-supported%20poly%28hydroxamic%20acid%29-cu%28II%29%20complex%20for%20ullmann%20etherification%20FULL%20TEXT.pdf https://eprints.ums.edu.my/id/eprint/27248/2/Highly%20active%20cellulose-supported%20poly%28hydroxamic%20acid%29-cu%28II%29%20complex%20for%20ullmann%20etherification%20ABSTRACT.pdf https://eprints.ums.edu.my/id/eprint/27248/ https://pubs.acs.org/doi/pdf/10.1021/acsomega.0c05840 https://dx.doi.org/10.1021/acsomega.0c05840 |
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| Summary: | Highly active natural pandanus-extracted cellulose-supported poly(hydroxamic acid)−Cu(II) complex 4 was synthesized. The surface of pandanus cellulose was modified through graft copolymerization using purified methyl acrylate as a monomer. Then, copolymer methyl acrylate was converted into a bidentate chelating ligand poly(hydroxamic acid) via a Loosen rearrangement in the presence of an aqueous solution of hydroxylamine. Finally, copper species were incorporated into poly- (hydroxamic acid) via the adsorption process. Cu(II) complex 4 was fully characterized by Fourier transform infrared (FTIR), field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray (EDX), transmission electron microscopy (TEM), inductively coupled plasma optical emission spectrometry (ICP-OES), thermogravimetric analysis (TGA), X-ray diffraction (XRD), and X-ray photoelectron spectroscopy (XPS) analyses. The cellulose-supported Cu(II) complex 4 was successfully applied (0.005 mol %) to the Ullmann etherification of aryl, benzyl halides, and phenacyl bromide with a number of aromatic phenols to provide the corresponding ethers with excellent yield [benzyl halide (70−99%); aryl halide (20−90%)]. Cu(II) complex 4 showed high stability and was easily recovered from the reaction mixture. It could be reused up to seven times without loss of its original catalytic activity. Therefore, Cu(II) complex 4 can be commercially utilized for the preparation of various ethers, and this synthetic technique could be a part in the synthesis of natural products and medicinal compounds. |
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