Copper-Catalyzed Trifluoromethylation and Cyclization of Aromatic-Sulfonyl-Group-Tethered Alkenes for the Construction of 1,2-Benzothiazinane Dioxide Type Compounds

被引：64
|
作者：
Dong, Xiang [1 ]
Sang, Rui [1 ]
Wang, Qiang [1 ,2 ,3 ]
Tang, Xiang-Ying [1 ]
Shi, Min [1 ,2 ,3 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[2] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China
[3] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 50期
基金：
中国国家自然科学基金;
关键词：
benzothiazinane; copper; homogeneous catalysis; radicals; trifluoromethylation; ALPHA; BETA-UNSATURATED CARBOXYLIC-ACIDS; OXIDATIVE TRIFLUOROMETHYLATION; TERMINAL ALKENES; 1,1-DIOXIDE; FLUORINE;
D O I：
10.1002/chem.201303623
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A multi-talented system: An efficient copper-catalyzed tandem trifluoromethylation/annulation of an electron-deficient aromatic ring has been developed. This method provides a powerful and straightforward way to synthesize trifluoromethylated 1,2-benzothiazinane dioxides under mild conditions (see scheme). The mechanism was investigated by a series of kinetic experiments and isotopic labeling studies. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：16910 / 16915
页数：6
相关论文
共 13 条
  • [1] Copper-Catalyzed 1,2-Dicarbonylative Cyclization of Alkenes with Alkyl Bromides via Radical Cascade Process
    Zhao, Fengqian
    Gu, Xing-Wei
    Franke, Robert
    Wu, Xiao-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (49)
  • [2] Copper-Catalyzed 1,2-Trifluoromethylation Carbonylation of Unactivated Alkenes: Efficient Access to β-Trifluoromethylated Aliphatic Carboxylic Acid Derivatives
    Wu, Fu-Peng
    Yuan, Yang
    Wu, Xiao-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (49) : 25787 - 25792
  • [3] Synthesis of Functionalized 1H-Indenes via Copper-Catalyzed Arylative Cyclization of Arylalkynes with Aromatic Sulfonyl Chlorides
    Zeng, Xiaoming
    Ilies, Laurean
    Nakamura, Eiichi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (44) : 17638 - 17640
  • [4] Copper-Catalyzed Intermolecular 1,2-Carbotriazolization of Alkenes with N-Sulfonyl-1,2,3-Triazoles and Aldehydes
    Ji, Jian
    Hu, Zongjing
    Guan, Cong
    Liu, Jinhua
    Deng, Yaqi
    Chen, Xuwen
    Liu, Shunying
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2023, 11 (45) : 16240 - 16248
  • [5] A Copper-Catalyzed Tandem Cyclization Reaction of Aminoalkynes with Alkynes for the Construction of Tetrahydropyrrolo[1,2-a]quinolines Scaffold
    Ma, Can-Liang
    Zhao, Jin-Hao
    Yang, Yong
    Zhang, Min-Kui
    Shen, Chao
    Sheng, Rong
    Dong, Xiao-Wu
    Hu, Yong-Zhou
    SCIENTIFIC REPORTS, 2017, 7
  • [6] A Copper-Catalyzed Tandem Cyclization Reaction of Aminoalkynes with Alkynes for the Construction of Tetrahydropyrrolo[1,2-a]quinolines Scaffold
    Can-Liang Ma
    Jin-Hao Zhao
    Yong Yang
    Min-Kui Zhang
    Chao Shen
    Rong Sheng
    Xiao-Wu Dong
    Yong-Zhou Hu
    Scientific Reports, 7
  • [7] Facile Construction of Tetrahydropyrrolizines by Iron-Catalyzed Double Cyclization of Alkene-Tethered Oxime Esters with 1,2-Disubstituted Alkenes
    Shimbayashi, Takuya
    Nakamoto, Daiki
    Okamoto, Kazuhiro
    Ohe, Kouichi
    ORGANIC LETTERS, 2018, 20 (10) : 3044 - 3048
  • [8] Copper-Catalyzed [3+2+1] Cycloaddition of Alkenes with Benzoquinones and Dicarbonyl Compounds via Tandem Oxidative Dicarbofunctionalization/Cyclization Sequence
    Du, Tianxing
    Li, Song
    He, Yunfei
    Long, Huan
    Liu, Xigong
    Li, Hai-Bei
    Liu, Lei
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (14) : 1681 - 1686
  • [9] Copper-Catalyzed Radical Cascade Cyclization of N-Substituted Indole-3-Aldehydes with Aryl Alkenes: Access to Pyrrolo[1,2-a]indole Scaffolds
    Cheng, Weibo
    Sun, Junzheng
    Liu, Changji
    Zhong, Yidong
    Xia, Chengcai
    Yang, Wenjing
    JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (03): : 1367 - 1375
  • [10] Copper-catalyzed tandem Ullmann type C-N coupling and dehydrative cyclization: synthesis of imidazo[1,2-c]quinazolines
    Nandwana, Nitesh K.
    Dhiman, Shiv
    Shelke, Ganesh M.
    Kumar, Anil
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (05) : 1736 - 1741
12