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Highly Active Cellulose-Supported Poly(hydroxamic acid)–Cu(II) Complex for Ullmann Etherification

2021; American Chemical Society; Volume: 6; Issue: 10 Linguagem: Inglês

10.1021/acsomega.0c05840

2470-1343

Choong Jian Fui, Tang Xin Ting, Mohd Sani Sarjadi, Zarina Amin, Shaheen M. Sarkar, Baba Musta, MdLutfor Rahman,

Nanomaterials for catalytic reactions

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.