Visible-light-promoted three-component cycloaddition reaction: synthesis of 4-functionalized 1,5-disubstituted 1,2,3-triazoles

被引：8
作者：
Kumar, Atul [1 ]
Kumar, Navaneet [1 ,2 ]
Bhadoria, Deepak [1 ,2 ]
机构：
[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Sect 10,Sitapur Rd,POB 173 Lucknow, Lucknow 226031, Uttar Pradesh, India
[2] Acad Sci & Innovat Res, Ghaziabad 201002, India
来源：
GREEN CHEMISTRY | 2021年 / 23卷 / 20期
关键词：
AZIDE-ALKYNE CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; CATALYZED CYCLOADDITION; TERMINAL ALKYNES; DIRECT ACCESS; IODINE; CYCLIZATION; SULFONES;
D O I：
10.1039/d1gc02328d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first visible-light promoted and photocatalyst-free three-component reaction protocol has been developed to synthesize 4-functionalized 1,5-disubstituted 1,2,3-triazoles from terminal alkynes, aryl azides, and arylsulfinic acid sodium salts or arylsulfonyl hydrazides in an aqueous medium at room temperature. Notably, the reaction proceeds seamlessly without using any transition-metal catalysts, ligands, or photocatalysts, and also reduces chemical waste. It also features an easy operation procedure, high regioselectivity, scalability, a broad substrate scope, mild reaction conditions, and good functional group tolerance.
引用
收藏
页码：7987 / 7995
页数：9
相关论文
共 110 条
  • [41] 1,2,3-Triazole in Heterocyclic Compounds, Endowed with Biological Activity, through 1,3-Dipolar Cycloadditions
    Lauria, Antonino
    Delisi, Riccardo
    Mingoia, Francesco
    Terenzi, Alessio
    Martorana, Annamaria
    Barone, Giampaolo
    Almerico, Anna Maria
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (16) : 3289 - 3306
  • [42] Chiral acid-catalysed enantioselective C-H functionalization of toluene and its derivatives driven by visible light
    Li, Fuyuan
    Tian, Dong
    Fan, Yifan
    Lee, Richmond
    Lu, Gang
    Yin, Yanli
    Qiao, Baokun
    Zhao, Xiaowei
    Xiao, Ziwei
    Jiang, Zhiyong
    [J]. NATURE COMMUNICATIONS, 2019, 10 (1)
  • [43] Photocatalyst-Free Visible-Light-Promoted C(sp2)-S Coupling: A Strategy for the Preparation of S-Aryl Dithiocarbamates
    Li, Guoqing
    Yan, Qiuli
    Gan, Ziyu
    Li, Qin
    Dou, Xiaomeng
    Yang, Daoshan
    [J]. ORGANIC LETTERS, 2019, 21 (19) : 7938 - 7942
  • [44] Photo-induced Metal-Catalyst-Free Aromatic Finkelstein Reaction
    Li, Lu
    Liu, Wenbo
    Zeng, Huiying
    Mu, Xiaoyue
    Cosa, Gonzalo
    Mi, Zetian
    Li, Chao-Jun
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (26) : 8328 - 8331
  • [45] Iodine-catalyzed diazo activation to access radical reactivity
    Li, Pan
    Zhao, Jingjing
    Shi, Lijun
    Wang, Jin
    Shi, Xiaodong
    Li, Fuwei
    [J]. NATURE COMMUNICATIONS, 2018, 9
  • [46] Visible-light-induced decarboxylative sulfonylation of cinnamic acids with sodium sulfinates by using Merrifield resin supported Rose Bengal as a catalyst
    Li, Pinhua
    Wang, Guan-Wu
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (22) : 5578 - 5585
  • [47] Direct access to 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of allyl ketones with azides
    Li, Wenjun
    Du, Zhiyun
    Huang, Jiayao
    Jia, Qianfa
    Zhang, Kun
    Wang, Jian
    [J]. GREEN CHEMISTRY, 2014, 16 (06) : 3003 - 3006
  • [48] Direct access to triazole-olefins through catalytic cycloaddition of azides to unsaturated aldehydes
    Li, Wenjun
    Jia, Qianfa
    Du, Zhiyun
    Wang, Jian
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (86) : 10187 - 10189
  • [49] Photoinducible Bioorthogonal Chemistry: A Spatiotemporally Controllable Tool to Visualize and Perturb Proteins in Live Cells
    Lim, Reyna K. V.
    Lin, Qing
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (09) : 828 - 839
  • [50] Azirine ligation: fast and selective protein conjugation via photoinduced azirine-alkene cycloaddition
    Lim, Reyna K. V.
    Lin, Qing
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (42) : 7993 - 7995
12345678910