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
  • [21] Copper-catalyzed α-selective C–H trifluoromethylation of acrylamides with TMSCF3
    Shang-Zheng Sun
    Hui Xu
    Hui-Xiong Dai
    [J]. Chinese Chemical Letters, 2019, 30 (05) : 969 - 972
  • [22] A Simple and Efficient Copper-Catalyzed Synthesis of N-Alkynylimidazoles
    Wang, Man-Gang
    Wu, Jun
    Shang, Zhi-Cai
    [J]. SYNLETT, 2012, (04) : 589 - 594
  • [23] Copper-Catalyzed Synthesis of N-Formyl/Acylsulfenamides and -thiosulfonamides
    Lee, Chan
    Lim, Yu Na
    Jang, Hye-Young
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (27) : 5934 - 5938
  • [24] Thioisomunchnones versus Acrylamides via Copper-Catalyzed Reaction of Thioamides with Diazocarbonyl Compounds
    Ilkin, Vladimir G.
    Filimonov, Valeriy O.
    Seliverstova, Eugenia A.
    Novikov, Mikhail S.
    V. Beryozkina, Tetyana
    Gagarin, Aleksey A.
    Belskaya, Nataliya P.
    Muthipeedika, Nibin Joy
    Bakulev, Vasiliy A.
    Dehaen, Wim
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (18): : 12196 - 12213
  • [25] Copper-Catalyzed Selective Electron Transfer Enables Switchable Divergent Synthesis of 3-Functionalized Oxindoles
    Jiang, Shu-Yun
    Shi, Jun
    Wang, Wei
    Sun, Yan-Zheng
    Wu, Wei
    Song, Jun-Rong
    Yang, Xiaoyan
    Hao, Ge-Fei
    Pan, Wei-Dong
    Ren, Hai
    [J]. ACS CATALYSIS, 2023, 13 (05) : 3085 - 3092
  • [26] Copper-Catalyzed Cyanoisopropylalkenylation of N-Alkenyl-acrylamides to Give 1,3-Dihydropyrrol-2-ones
    Dai, Enrui
    Luo, Qing
    Chen, Chunlin
    Ying, Fengyuan
    Dong, Ying
    Liu, Yingjie
    Wang, Baoling
    Ma, Yinhai
    Liang, Deqiang
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (12) : 3524 - 3531
  • [27] Anionic Bisoxazoline Ligands Enable Copper-Catalyzed Asymmetric Radical Azidation of Acrylamides
    Wu, Lianqian
    Zhang, Zhihan
    Wu, Dunqi
    Wang, Fei
    Chen, Pinhong
    Lin, Zhenyang
    Liu, Guosheng
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (13) : 6997 - 7001
  • [28] Copper-Catalyzed Oxidative Dearomatized Oxyalkylation of Indoles with Alcohols: Synthesis of 3-Alkoxy-2-Oxindoles
    Zhao, Dengyang
    Pan, Yingjie
    Guo, Shengkun
    Chen, Xiaoyun
    Hou, Hong
    Han, Ying
    Yan, Chaoguo
    Shi, Yaocheng
    Zhu, Shaoqun
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (24): : 16867 - 16872
  • [29] Copper-Catalyzed Selective Electron Transfer Enables Switchable Divergent Synthesis of 3-Functionalized Oxindoles
    Jiang, Shu-Yun
    Shi, Jun
    Wang, Wei
    Sun, Yan-Zheng
    Wu, Wei
    Song, Jun-Rong
    Yang, Xiaoyan
    Hao, Ge-Fei
    Pan, Wei-Dong
    Ren, Hai
    [J]. ACS CATALYSIS, 2023, : 3085 - 3092
  • [30] Catalyst-free direct arylsulfonylation of N-arylacrylamides with sulfinic acids: a convenient and efficient route to sulfonated oxindoles
    Wei, Wei
    Wen, Jiangwei
    Yang, Daoshan
    Du, Juan
    You, Jinmao
    Wang, Hua
    [J]. GREEN CHEMISTRY, 2014, 16 (06) : 2988 - 2991