Efficient one-pot click synthesis of β-hydroxy-1,2,3-triazoles catalyzed by copper(I)@phosphorated SiO2 via multicomponent reaction in aqueous media

被引:54
|
作者
Naeimi, Hossein [1 ]
Nejadshafiee, Vajihe [1 ]
机构
[1] Univ Kashan, Dept Organ Chem, Fac Chem, Kashan 87317, Iran
关键词
COPPER NANOPARTICLES; 1,2,3-TRIAZOLES; WATER; CHEMISTRY; CARBON; AZIDE; CYCLOADDITION; EPOXIDES;
D O I
10.1039/c4nj00909f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Copper(I)-modified SiO2, in particular Cu(I)@phosphorated SiO2 (CPSi) has been found to effectively catalyze the multi-component synthesis of beta-hydroxy-1,2,3-triazoles from a variety of epoxides and alkynes in water. This novel heterogeneous catalyst is easily recycled and reused several times. The formation of the product proceeds in two reaction steps in one pot through a mechanism that involves in situ generated organic azide intermediate, followed by rapid ring closure of this intermediate with terminal alkynes to form b-hydroxy-1,2,3-triazole derivatives. The pure products were obtained in significantly high yields and short reaction times.
引用
收藏
页码:5429 / 5435
页数:7
相关论文
共 50 条
  • [1] Synthesis of ferrocenyl based β-hydroxy-1,2,3-triazoles and study of electrochemical properties via click reaction
    Abbasi, Hassan
    Jadidi, Somayeh Rashtabad
    Teimuri-Mofrad, Reza
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2023, 985
  • [2] Copper(I)-Catalyzed Interrupted Click/Sulfenylation Cascade: One-Pot Synthesis of Sulfur Cycle Fused 1,2,3-Triazoles
    Wang, Weiguo
    Huang, Shuai
    Yan, Shikun
    Sun, Xuejun
    Tung, Chen-Ho
    Xu, Zhenghu
    CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (05) : 445 - 448
  • [3] Alkenes as Azido Precursors for the One-Pot Synthesis of 1,2,3-Triazoles Catalyzed by Copper Nanoparticles on Activated Carbon
    Alonso, Francisco
    Moglie, Yanina
    Radivoy, Gabriel
    Yus, Miguel
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (10) : 5031 - 5037
  • [4] Efficient Synthesis of 5-Trifluoromethylthio-1,2,3-Triazoles: One-Pot Multicomponent Reaction from Elemental Sulfur and TMSCF3
    Zhang, Lin-Lin
    Li, Meng-Tian
    Shen, Liang-Liang
    Wu, Qin-Pei
    SYNTHESIS-STUTTGART, 2020, 52 (02): : 304 - 310
  • [5] Nanocomposite copper metal as an efficient heterogeneous catalyst in click synthesis of 1,2,3-triazoles in aqueous media
    Nejadshafiee, Vajhe
    Naeimi, Hossein
    TURKISH JOURNAL OF CHEMISTRY, 2017, 41 (05) : 700 - +
  • [6] One-pot synthesis of 1,2,3-triazoles from Michael reaction
    Korea Research Institute of Chemical Technology, Daejeon 305-343, Korea, Republic of
    不详
    Bull. Korean Chem. Soc., 2008, 4 (723-724): : 723 - 724
  • [7] New routes to Cu(I)/Cu nanocatalysts for the multicomponent click synthesis of 1,2,3-triazoles
    Abdulkin, Pavel
    Moglie, Yanina
    Knappett, Benjamin R.
    Jefferson, David A.
    Yus, Miguel
    Alonso, Francisco
    Wheatley, Andrew E. H.
    NANOSCALE, 2013, 5 (01) : 342 - 350
  • [8] One-pot synthesis of 1,2,3-triazoles from Michael reaction
    Lee, Ihl Young Choi
    Yu, Ok Jong
    Lim, Hee-Jeong
    Lee, Hyo Won
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2008, 29 (04): : 723 - 724
  • [9] Copper-Catalyzed Synthesis of 4-CF3-1,2,3-Triazoles: An Efficient and Facile Approach via Click Reaction
    Tang, Tinghong
    Chen, Cuiting
    Fu, Xin
    Xu, Huilan
    Wu, Luyong
    Chen, Wenhao
    MOLECULES, 2024, 29 (06):
  • [10] One-pot sequential synthesis of β-hydroxy-1,4-disubstituted-1,2,3-triazoles from in-situ generated β-azido alcohol by click chemistry
    Reddy, K. Rajender
    Maheswari, C. Uma
    Rajgopal, K.
    Kantam, M. Lakshmi
    SYNTHETIC COMMUNICATIONS, 2008, 38 (13) : 2158 - 2167