Articles

Cross-Linked Chitosan Bead Supported Copper Complex in Water as a Green and Efficient Catalytic Protocol for Ullmann Reaction

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  • a Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027;
    b School of Chemical and Biomedical Engineering, College of Engineering, Nanyang Technological University, 62 Nanyang Drive, Singapore 637459, Singapore

Received date: 2019-01-14

  Revised date: 2019-03-25

  Online published: 2019-04-11

Supported by

Project supported by the National Natural Science Foundation of China (No. 21476194), and the National Key Research and Development Program of China (No. 2016YFB0301800).

Abstract

A green, efficient, and recyclable catalytic protocol for Ullmann C-N reaction in water was developed. The catalyst Chi-Gly@CuI was prepared by the cross-linking reaction of chitosan bead with glyoxal and subsequently anchored with copper salt. Chi-Gly@CuI bead of 0.3 mm in mean diameter possesses porous micro-structure demonstrated by scanning electron microscope (SEM). The structure of Chi-Gly@CuI was characterized by Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TG), X-ray diffraction (XRD), inductively coupled plasma-atomic emission spectrometry (ICP-AES), and X-ray photoelectron spectroscopy (XPS). This catalytic protocol for Ullmann reaction in water exhibited high applicability, from which the corresponding coupling products were afforded in good to excellent yields. Chi-Gly@CuI could be easily separated from products by simple filtration almost without weight loss. Most notably, after 10 times of recycling, its catalytic activity and chemical stability were still maintained.

Cite this article

Lü Xiaomei, Ruan Jiancheng, Chen Xinzhi, Qian Chao . Cross-Linked Chitosan Bead Supported Copper Complex in Water as a Green and Efficient Catalytic Protocol for Ullmann Reaction[J]. Chinese Journal of Organic Chemistry, 2019 , 39(6) : 1720 -1726 . DOI: 10.6023/cjoc201901018

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