Copper-catalyzed arylsulfonylation of N-arylsulfonyl-acrylamides with arylsulfonohydrazides: synthesis of sulfonated oxindoles

被引:56
|
作者
Tian, Qingshan [1 ]
He, Ping [1 ]
Kuang, Chunxiang [1 ,2 ]
机构
[1] Tongji Univ, Dept Chem, Shanghai 200092, Peoples R China
[2] Minist Educ, Key Lab Yangtze River Water Environm, Shanghai 200092, Peoples R China
关键词
ACTIVATED ALKENES; HIGHLY EFFICIENT; VINYL SULFONES; BOND FORMATION; 3-COMPONENT OXYTRIFLUOROMETHYLATION; AEROBIC DIFUNCTIONALIZATION; ARYL ACRYLAMIDES; TRIFLUOROMETHYLATION; SULFONYLHYDRAZIDES; AMINOTRIFLUOROMETHYLATION;
D O I
10.1039/c4ob01231c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed arylsulfonylation of N-arylsulfonyl-acrylamides with sulfonylhydrazides through a tandem radical process was developed. This methodology provided an alternative strategy for the synthesis of sulfonated oxindoles by forming C-S, C-N and C-C bonds in a single operation.
引用
收藏
页码:6349 / 6353
页数:5
相关论文
共 50 条
  • [1] Copper-Catalyzed Arylsulfonylation and Cyclizative Carbonation of N-(Arylsulfonyl)acrylamides Involving Desulfonative Arrangement toward Sulfonated Oxindoles
    Wang, Hepan
    Sun, Song
    Cheng, Jiang
    [J]. ORGANIC LETTERS, 2017, 19 (21) : 5844 - 5847
  • [2] Copper-Catalyzed Oxidative Electrophilic Carbofunctionalization of Acrylamides for the Synthesis of Oxindoles
    Li, Xueqin
    Xu, Jian
    Zhang, Pengbo
    Gao, Yuzhen
    Wu, Ju
    Tang, Guo
    Zhao, Yufen
    [J]. SYNLETT, 2014, 25 (14) : 2009 - 2012
  • [3] Synthesis of Sulfonated Oxindoles by Potassium Iodide Catalyzed Arylsulfonylation of Activated Alkenes with Sulfonylhydrazides in Water
    Li, Xiaoqing
    Xu, Xiangsheng
    Hu, Peizhu
    Xiao, Xuqiong
    Zhou, Can
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14): : 7343 - 7348
  • [4] Copper-catalyzed N-arylation of oxindoles
    Phillips, Dean P.
    Hudson, Andrew R.
    Nguyen, Bao
    Lau, Thomas L.
    McNeill, Matthew H.
    Dalgard, Jackline E.
    Chen, Jyun-Hung
    Penuliar, Richard J.
    Miller, Todd A.
    Zhi, Lin
    [J]. TETRAHEDRON LETTERS, 2006, 47 (40) : 7137 - 7138
  • [5] Copper-Catalyzed Oxidative Benzylarylation of Acrylamides by Benzylic C-H Bond Functionalization for the Synthesis of Oxindoles
    Zhou, Shi-Liu
    Guo, Li-Na
    Wang, Hua
    Duan, Xin-Hua
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (39) : 12970 - 12973
  • [6] Efficient copper-catalyzed intramolecular N-arylation for the synthesis of oxindoles
    Jhan, Yu-Huei
    Kang, Ting-Wei
    Hsieh, Jen-Chieh
    [J]. TETRAHEDRON LETTERS, 2013, 54 (09) : 1155 - 1159
  • [7] Copper-catalyzed hydroboration of alkenyl oxindoles
    Contreira, Maria Eduarda
    Ludtke, Diogo S.
    Moro, Angelica, V
    [J]. TETRAHEDRON LETTERS, 2018, 59 (29) : 2784 - 2787
  • [8] Copper-Catalyzed Radical-Promoted Aminocyclization of Acrylamides with N-Fluorobenzenesulfonimide
    Xia, Xiao-Feng
    Zhu, Su-Li
    Liu, Jian-Biao
    Wang, Dawei
    Liang, Yong-Min
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24): : 12482 - 12488
  • [9] An efficient synthesis of 4-bromo-N-substituted oxindoles by an intramolecular copper-catalyzed amidation reaction
    van den Hoogenband, Adri
    Lange, Jos H. M.
    den Hartog, Jack A. J.
    Henzen, Remco
    Terpstra, Jan Willem
    [J]. TETRAHEDRON LETTERS, 2007, 48 (26) : 4461 - 4465
  • [10] Copper-Catalyzed Regioselective Sulfenylation of Indoles with Arylsulfonyl Chlorides
    Wu, Zhimeng
    Li, Yan-Chun
    Ding, Wen-Zhang
    Zhu, Tao
    Liu, Shao-Zhong
    Ren, Xuehong
    Zou, Liang-Hua
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (05) : 625 - 628