Copper catalysts supported by dehydroacetic acid chitosan schiff base for CuAAC click reaction in water

被引:1
|
作者
Asadi, Sahar [1 ]
Bahramian, Bahram [1 ]
Khalaji, Aliakbar Dehno [2 ]
Mirdarvatan, Vahid [1 ]
Bakherad, Mohammad [1 ]
Rezaeifard, Amin [1 ]
机构
[1] Shahrood Univ Technol, Dept Chem, Shahrood, Iran
[2] Golestan Univ, Fac Sci, Dept Chem, Gorgan, Iran
关键词
Chitosan schiff base; 1,2,3-triazoles; Azide-alkyne cycloaddition; Click chemistry; Dehydroacetic acid; CuAAC reaction; EFFICIENT HETEROGENEOUS CATALYST; O-CARBOXYMETHYL CHITOSAN; MAGNETICALLY-RECOVERABLE CATALYST; 3+2 CYCLOADDITION REACTION; RECYCLABLE CATALYST; HUISGEN CYCLOADDITION; PD(II) COMPLEXES; HIGHLY EFFICIENT; ALKYNE; AZIDE;
D O I
10.1007/s10570-024-05840-w
中图分类号
TB3 [工程材料学]; TS [轻工业、手工业、生活服务业];
学科分类号
0805 ; 080502 ; 0822 ;
摘要
The synthesis of 1,4-disubstituted 1,2,3-triazoles through copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction has gained much attention due to its versatility and broad range of applications. In this study, we report two novel heterogeneous copper catalysts based on dehydroacetic acid chitosan Schiff base (DCSB) for the CuAAC reaction in water. The DCSB was synthesized through the condensation reaction of dehydroacetic acid and chitosan, and was subsequently used to support Cu(II) ions and CuO nanoparticles (CuO NPs). The prepared compounds were characterized using FT-IR, XRD, FE-SEM, EDX, BET, and TGA analyses. The performance of the catalysts was evaluated in a model reaction involving the 1,3-dipolar cycloaddition reaction of benzyl chloride, phenylacetylene, and sodium azide for the synthesis of 1,2,3-triazoles. After optimizing the reaction conditions, the scope of the reaction was extended to various substituted benzyl chlorides and alkyne molecules. Moreover, the recyclability of the catalysts was studied for up to four cycles.
引用
收藏
页码:3497 / 3516
页数:20
相关论文
共 50 条
  • [41] Fiber-Supported Acid-Base Bifunctional Catalysts for Efficient Nucleophilic Addition in Water
    Du, Jianguo
    Tao, Minli
    Zhang, Wenqin
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2016, 4 (08): : 4296 - 4304
  • [42] Synthesis of water soluble PEGylated (copper) phthalocyanines via Mitsunobu reaction and Cu(I)-catalysed azide-alkyne cycloaddition (CuAAC) "click" chemistry
    Li, Muxiu
    Khoshdel, Ezat
    Haddleton, David M.
    POLYMER CHEMISTRY, 2013, 4 (16) : 4405 - 4411
  • [43] Chiral copper(II)-Schiff base complexes as catalysts for asymmetric cyclopropanation of styrene
    Qiu, M
    Liu, GS
    Yao, XQ
    Guo, MY
    Pan, GZ
    Zheng, Z
    CHINESE JOURNAL OF CATALYSIS, 2001, 22 (01) : 77 - 80
  • [44] Chiral copper-Schiff base catalyst for asymmetric henry reaction
    Yong-guang Gao
    Na Chen
    Hua-jiang Wu
    Xin-sheng Li
    Russian Journal of Organic Chemistry, 2007, 43 : 1754 - 1756
  • [45] Chiral copper-Schiff base catalyst for asymmetric Henry reaction
    Gao, Yong-guang
    Chen, Na
    Wu, Hua-jiang
    Li, Xin-sheng
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (12) : 1754 - 1756
  • [46] Development of a novel folic acid chitosan supported imidazole Schiff base for tumor targeted gene delivery system and drug therapy
    Shi, Bingyang
    Zhang, Mengjue
    Bi, Jingxiu
    Dai, Sheng
    JOURNAL OF CONTROLLED RELEASE, 2013, 172 (01) : E98 - E98
  • [47] Copper(I)-Catalyzed Alkyne-Azide Cycloaddition (CuAAC) "Click" Reaction: A Powerful Tool for Functionalizing Polyhydroxylated Platforms
    Pineda-Castaneda, Hector Manuel
    Rivera-Monroy, Zuly Jenny
    Maldonado, Mauricio
    ACS OMEGA, 2023,
  • [48] Alkylaluminium complexes supported by Schiff base as pre-catalysts in hydroboration of alkynes and nitriles
    Yan, Ben
    Pang, Ziyuan
    Ma, Xiaoli
    Yang, Zhi
    INORGANICA CHIMICA ACTA, 2024, 569
  • [49] EnantioselectiveAza-DielsAlder reaction catalyzed by clay supported Schiff base complex†
    Kannan, V.
    Sreekumar, K.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2021, 58 (01) : 153 - 160
  • [50] Cyclopropanation of styrene catalyzed by chitosan Schiff-base copper (II) heterogeneous catalyst
    Sun, W
    Xia, CG
    Wang, AQ
    ACTA CHIMICA SINICA, 2002, 60 (01) : 162 - 165