Three-component assembly of 5-halo-1,2,3-triazoles via aerobic oxidative halogenation

被引：19
|
作者：
Li, Lingjun [1 ]
Hao, Guoliang [1 ]
Zhu, Anlian [1 ]
Liu, Sangui [1 ]
Zhang, Guisheng [1 ]
机构：
[1] Henan Normal Univ, Sch Chem & Chem Engn, Minist Educ, Key Lab Green Chem Media & React, Xinxiang 453007, Peoples R China
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 45期
关键词：
Aerobic oxidative halogenations; 5-Halo-1,2,3-triazole; Nucleoside; CLICK CHEMISTRY; AZIDE; CYCLOADDITION; NUCLEOTIDE; COMPLEXES; OXYGEN; ROUTE; METAL;
D O I：
10.1016/j.tetlet.2013.08.089
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An effective synthetic protocol for 5-halo-1,2,3-triazoles was developed by novel TBDMSCI (tert-butyldi-methylsily1 chloride)-activated aerobic oxidative halogenations in this Letter. TBDMSCI, for the first time, was found to activate aerobic oxidation of CuX to produce X-2 with Cu+ which then could effectively promote one-pot syntheses of 5-halo-1,2,3-triazole from alkyne, azide, and CuX (X = I, Br) under O-2 atmosphere at room temperature. The advantages in this method include inexpensive and green O-2 as oxidant, use of mild and non-oxidative additive, and wide scope of substrates. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6057 / 6060
页数：4
相关论文
共 50 条
  • [31] Practical one-pot synthesis of 5-alkynyl-1,2,3-triazoles via heterogeneous copper(I)-catalyzed tandem three-component click/alkynylation reaction
    Zhao, Ruonan
    Liao, Yang
    Yan, Tao
    Cai, Mingzhong
    APPLIED ORGANOMETALLIC CHEMISTRY, 2020, 34 (01)
  • [32] Nano-copper catalyzed three-component reaction to construct 1,4-substituted 1,2,3-triazoles
    Huang, Lina
    Liu, Wei
    Wu, Juncheng
    Fu, Ying
    Wang, Kehu
    Huo, Congde
    Du, Zhengyin
    TETRAHEDRON LETTERS, 2014, 55 (14) : 2312 - 2316
  • [33] Copper-catalyzed cross-coupling reactions of 5-stibano-1,2,3-triazoles with bromoalkynes under aerobic conditions: Synthesis of 5-alkynyl-1,2,3-triazoles
    Yamada, Mizuki
    Matsuura, Daiki
    Hasegawa, Mai
    Murata, Yuki
    Kakusawa, Naoki
    Matsumura, Mio
    Yasuike, Shuji
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 871 : 79 - 85
  • [34] Computational studies on CuAAC reaction mechanism with [CuX(PPh3)]; X = I, Br, Cl for the synthesis of 4- and 5-halo-1,2,3-triazoles
    Ali A. Khairbek
    Abdullah Y. Alzahrani
    Mohammad Abd Al-Hakim Badawi
    Renjith Thomas
    Reaction Kinetics, Mechanisms and Catalysis, 2024, 137 : 777 - 790
  • [35] Regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles via three-component coupling of secondary alcohols, TMSN3 and alkynes
    Sreedhar, B.
    Reddy, P. Surendra
    Krishna, V. Rama
    TETRAHEDRON LETTERS, 2007, 48 (33) : 5831 - 5834
  • [36] Computational studies on CuAAC reaction mechanism with [CuX(PPh3)]; X = I, Br, Cl for the synthesis of 4-and 5-halo-1,2,3-triazoles
    Khairbek, Ali A.
    Alzahrani, Abdullah Y.
    Badawi, Mohammad Abd Al-Hakim
    Thomas, Renjith
    REACTION KINETICS MECHANISMS AND CATALYSIS, 2024, 137 (02) : 777 - 790
  • [37] Synthesis of Fully Functionalized 5-Selanyl-1,2,3-triazoles: Copper-Catalysed Three-Component Reaction of Ethynylstibanes, Organic Azides, and Diaryl Diselenides
    Yamada, Mizuki
    Matsumura, Mio
    Takino, Fumina
    Murata, Yuki
    Kurata, Yuka
    Kawahata, Masatoshi
    Yamaguchi, Kentaro
    Kakusawa, Naoki
    Yasuike, Shuji
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (02) : 170 - 177
  • [38] μ-Hydroxyl trinuclear copper(II) clusters: reactivity and unusual formation in the three-component synthesis of 1,2,3-triazoles in aqueous media
    Cai, Yuan-Bo
    Liang, Lei
    Zhang, Jing
    Sun, Hao-Ling
    Zhang, Jun-Long
    DALTON TRANSACTIONS, 2013, 42 (15) : 5390 - 5400
  • [39] A Metal-Free Three-Component Reaction for the Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles
    Thomas, Joice
    John, Jubi
    Parekh, Nikita
    Dehaen, Wim
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) : 10155 - 10159
  • [40] Copper(I)-Catalyzed Three-Component Coupling of N-Tosylhydrazones, Alkynes and Azides: Synthesis of Trisubstituted 1,2,3-Triazoles
    Zhang, Zhikun
    Zhou, Qi
    Ye, Fei
    Xia, Ying
    Wu, Guojiao
    Hossain, Mohammad Lokman
    Zhang, Yan
    Wang, Jianbo
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) : 2277 - 2286
12345