Metal-free TBAI-catalyzed arylsulfonylation of activated alkenes with sulfonylhydrazides

被引:59
|
作者
Yu, Wubin [1 ]
Hu, Peizhu [1 ]
Fan, Yuanyuan [1 ]
Yu, Congyao [1 ]
Yan, Xinhuan [1 ]
Li, Xiaoqing [1 ]
Xu, Xiangsheng [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
TERT-BUTYL HYDROPEROXIDE; N-ARYL ACRYLAMIDES; AEROBIC DIFUNCTIONALIZATION; OXIDATIVE AMINATION; TERMINAL ALKYNES; C(SP(3))-H BONDS; C-N; OXINDOLES; FUNCTIONALIZATION; ESTERIFICATION;
D O I
10.1039/c4ob01651c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient metal-free oxidative arylsulfonylation of alpha,beta-unsaturated imides with sulfonylhydrazides leading to isoquinoline-1,3(2H,4H)-dione derivatives has been developed. The procedure involves the generation of sulfonyl radicals via cleavage of the S-N bond of sulfonylhydrazides with sulfonylation and C-H functionalization. The protocol uses the economical and environmentally friendly TBAI-TBHP catalytic system, and the corresponding isoquinoline-1,3(2H,4H)-diones with various functional groups were obtained in moderate to good yields.
引用
收藏
页码:3308 / 3313
页数:6
相关论文
共 50 条
  • [1] 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
  • [2] Direct and metal-free arylsulfonylation of alkynes with sulfonylhydrazides for the construction of 3-sulfonated coumarins
    Wei, Wei
    Wen, Jiangwei
    Yang, Daoshan
    Guo, Mengyuan
    Wang, Yingying
    You, Jinmao
    Wang, Hua
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (04) : 768 - 771
  • [3] Iron-Catalyzed Arylsulfonylation of Activated Alkenes
    Shi, Liangliang
    Wang, Hui
    Yang, Haijun
    Fu, Hua
    [J]. SYNLETT, 2015, 26 (05) : 688 - 694
  • [4] Metal-Free Aryltrifluoromethylation of Activated Alkenes
    Kong, Wangqing
    Casimiro, Maria
    Fuentes, Noelia
    Merino, Estibaliz
    Nevado, Cristina
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (49) : 13086 - 13090
  • [5] TBAI-Catalyzed S-H and N-H Insertion Reactions of α-Diazoesters with Thiophenols and Amines under Metal-Free Conditions
    Chen, Rongxiang
    Ma, Guoyang
    Li, Yawen
    Zhang, Jinju
    Xia, Ran
    Wang, Kai-Kai
    Liu, Lantao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (16): : 10990 - 10999
  • [6] Metal-free catalyzed arylsulfonylation of chloroquinoline with sodium arylsulfinates under microwave irradiation
    Li, Xi-Yong
    Sun, Ya-Min
    Yuan, Jin-Wei
    [J]. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2018, 73 (05): : 295 - 303
  • [7] Synthesis of β-keto-sulfones via metal-free TBAI/TBHP mediated oxidative cross-coupling of vinyl acetates with sulfonylhydrazides
    Tang, Yucai
    Fan, Yuanyuan
    Gao, Hongjie
    Li, Xiaoqing
    Xu, Xiangsheng
    [J]. TETRAHEDRON LETTERS, 2015, 56 (41) : 5616 - 5618
  • [8] TBAI-Catalyzed/Water-Assisted Double C-S Bond Formations: An Efficient Approach to Sulfides through Metal-Free Three-Component Reactions
    Chu, Xue-Qiang
    Xu, Xiao-Ping
    Ji, Shun-Jun
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (40) : 14181 - 14185
  • [9] Transition Metal-Free Reduction of Activated Alkenes Using a Living Microorganism
    Brewster, Richard C.
    Suitor, Jack T.
    Bennett, Adam W.
    Wallace, Stephen
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (36) : 12409 - 12414
  • [10] An efficient synthesis of sulfonated quinoline diones by copper catalyzed sulfonylation of activated alkenes with sulfonylhydrazides
    Wang, Shucheng
    Huang, Xuhu
    Wang, Qi
    Ge, Zemei
    Wang, Xin
    Li, Runtao
    [J]. RSC ADVANCES, 2016, 6 (14): : 11754 - 11757