Highly Efficient Synthesis of 1,2,3-Triazoles Catalyzed by Silane Coupled Chitosan-CuBr Catalyst

doi:10.6023/cjoc201404024

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (10): 2068-2075.DOI: 10.6023/cjoc201404024 Previous Articles Next Articles

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硅烷偶联化壳聚糖负载CuBr高活性催化合成1,2,3-三唑化合物

江云兵, 王彦龙, 韩骞, 朱荣俊, 熊兴泉

华侨大学材料科学与工程学院厦门 361021

收稿日期:2014-04-14 修回日期:2014-05-20 发布日期:2014-06-09
通讯作者: 熊兴泉 E-mail:xxqluli@hqu.edu.cn
基金资助:
国家自然科学基金（No. 21004024）、福建省自然科学基金（No. 2011J01046）、福建省“高校新世纪优秀人才支持计划”（No. 2012FJ-NCET-ZR03）和福建省“高校杰出青年科研人才培育计划”（No. 11FJPY02）以及“华侨大学中青年教师科研提升资助计划”（No. ZQN-YX103）资助项目.

Highly Efficient Synthesis of 1,2,3-Triazoles Catalyzed by Silane Coupled Chitosan-CuBr Catalyst

Jiang Yunbing, Wang Yanlong, Han Qian, Zhu Rongjun, Xiong Xingquan

College of Materials Science and Engineering, Huaqiao University, Xiamen 361021

Received:2014-04-14 Revised:2014-05-20 Published:2014-06-09
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21004024), the Natural Science Foundation of Fujian Province (No. 2011J01046), the Program for New Century Excellent Talents in Fujian Province (No. 2012FJ-NCET-ZR03) and the University Distinguished Young Research Talent Training Program of Fujian Province (No. 11FJPY02) and the Promotion Program for Young and Middle-aged Teacher in Science and Technology Research of Huaqiao University (No. ZQN-YX103).

N-(2-Aminoethyl)-3-aminopropyltriethoxysilane-modified chitosan (CS-AAPTS) was successfully prepared by simply refluxing the corresponding CS and AAPTS in toluene solution. Subsequently, CS-AAPTS bound CuBr (CS-CuBr) was synthesized by the reaction of CS-AAPTS with CuBr in DMF at room temperature under N₂ atmosphere. The obtained catalyst was characterized by FT-IR, TGA, XRD and EDX. The catalytic performances were evaluated in one-pot multicomponent copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction under microwave-assisted condition. CS-CuBr was found to exhibit obvious catalytic activity to rapidly prepare 1,2,3-triazole compounds under the microwave irradiation power of 480 W and 70 ℃ operating conditions. Furthermore, the catalyst could be easily recovered by simple filtration and recycled at least 4 cycles without significant loss of activity, and the preparation of 1,2,3-triazoles could be scaled up to multiple-gram conveniently with a yield up to 94%.

Key words: chitosan, heterogeneous catalyst, microwave-assisted, one-pot, 1,2,3-triazoles, CuAAC reaction

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Jiang Yunbing, Wang Yanlong, Han Qian, Zhu Rongjun, Xiong Xingquan. Highly Efficient Synthesis of 1,2,3-Triazoles Catalyzed by Silane Coupled Chitosan-CuBr Catalyst[J]. Chin. J. Org. Chem., 2014, 34(10): 2068-2075.

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硅烷偶联化壳聚糖负载CuBr高活性催化合成1,2,3-三唑化合物

Highly Efficient Synthesis of 1,2,3-Triazoles Catalyzed by Silane Coupled Chitosan-CuBr Catalyst

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