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

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2021 Mar 22

PMID 33748590

Citations 1

Authors

Choong Jian Fui

Tang Xin Ting

Mohd Sani Sarjadi

Zarina Amin

Shaheen M Sarkar

Baba Musta

MdLutfor Rahman

Affiliations

Soon will be listed here.

Abstract

Highly active natural pandanus-extracted cellulose-supported poly(hydroxamic acid)-Cu(II) complex 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 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 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 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 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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