Electrochemical monofluoroalkylation cyclization of N-arylacrylamides to construct monofluorinated 2-oxindoles

被引:19
|
作者
Lv, Yanxia [1 ,2 ,3 ]
Hou, Zhong-Wei [1 ,2 ]
Wang, Yi [4 ]
Li, Pinhua [3 ]
Wang, Lei [1 ,2 ,3 ,4 ]
机构
[1] Taizhou Univ, Adv Res Inst, Taizhou 318000, Peoples R China
[2] Taizhou Univ, Sch Pharmaceut Sci, Taizhou 318000, Peoples R China
[3] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China
[4] Anhui Med Univ, Hosp 2, Hefei 230601, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
FLUORINATED 3,3-DISUBSTITUTED 2-OXINDOLES; C-H FUNCTIONALIZATION; RADICAL CYCLIZATION; CATALYST-FREE; ACCESS; BENZYLACRYLAMIDES; DERIVATIVES; TRIFLUOROMETHYLATION/CYCLIZATION; SPIROCYCLIZATION; OXINDOLES;
D O I
10.1039/d2ob01883g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An electrochemical monofluoroalkylation cyclization of N-arylacrylamides to synthesize monofluorinated 2-oxindoles has been developed, which employs common dimethyl 2-fluoromalonate as a monofluoroalkyl radical precursor and obviates the use of prefunctionalized monofluoroalkylation reagents and sacrificial oxidants. A variety of monofluorinated nitrogen-containing heterocyclic compounds were efficiently obtained with satisfactory yields from readily available materials.
引用
收藏
页码:1014 / 1020
页数:7
相关论文
共 50 条
  • [1] Synthesis of Seleno Oxindoles via Electrochemical Cyclization of N-arylacrylamides with Diorganyl Diselenides
    Wang, Xin-Yu
    Zhong, Yuan-Fang
    Mo, Zu-Yu
    Wu, Shi-Hong
    Xu, Yan-Li
    Tang, Hai-Tao
    Pan, Ying-Ming
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (01) : 208 - 214
  • [2] Photoredox-Catalyzed Tandem Radical Cyclization of N-Arylacrylamides: General Methods To Construct Fluorinated 3,3-Disubstituted 2-Oxindoles Using Fluoroalkylsulfonyl Chlorides
    Tang, Xiao-Jun
    Thomoson, Charles S.
    Dolbier, William R., Jr.
    ORGANIC LETTERS, 2014, 16 (17) : 4594 - 4597
  • [3] Copper-Promoted Aryldifluoromethylenation of N-Arylacrylamides to 3-Benzo-diazolyldifluoromethylene-Substituted 2-Oxindoles
    Zhang, Tiantian
    Chen, Bo
    Wang, Wei
    Zhang, Qian
    Wang, Pingyang
    Wan, Wen
    Deng, Hongmei
    Hao, Jian
    Jiang, Haizhen
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (05) : 671 - 674
  • [4] Electrochemical Trifluoromethylthiolation/Cyclization of N-Arylacrylamides with AgSCF3: Access to SCF3-Containing Oxindoles
    Wang, Yu
    Wang, Ye
    Wang, Sheng
    Yu, Zhou
    Wang, Siqi
    Chen, Wenbo
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (17): : 11950 - 11958
  • [5] Synthesis of difluoromethylated 2-oxindoles and quinoline-2,4-diones via visible light-induced tandem radical cyclization of N-arylacrylamides
    Sun, Huan
    Jiang, Yue
    Yang, Ying-Sha
    Li, Yun-Yun
    Li, Lin
    Wang, Wen-Xuan
    Feng, Tao
    Li, Zheng-Hui
    Liu, Ji-Kai
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (27) : 6629 - 6638
  • [6] Synthesis of Oxindoles via Iron-Mediated Hydrometallation-Cyclization of N-Arylacrylamides
    Gui, Qingwen
    Hu, Liang
    Chen, Xiang
    Liu, Jidan
    Tan, Ze
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (09) : 870 - 874
  • [7] Photoredox Cyclization of N-Arylacrylamides for Synthesis of Dihydroquinolinones
    Liu, Zhaosheng
    Zhong, Shuai
    Ji, Xiaochen
    Deng, Guo-Jun
    Huang, Huawen
    ORGANIC LETTERS, 2022, 24 (01) : 349 - 353
  • [8] A general route to fluorinated 3,3-disubstituted 2-oxindoles via a photoinduced radical cyclization of N-arylacrylamides under catalyst-free conditions
    An, Yuanyuan
    Li, Yuewen
    Wu, Jie
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (05): : 570 - 573
  • [9] Free Radical Cyclization of N-Arylacrylamides: Mild and Facile Synthesis of 3-Thiocyanato Oxindoles
    Karmaker, Pran Gopal
    Qiu, Jiashen
    Wu, Di
    Yin, Hongquan
    Chen, Fu-Xue
    SYNLETT, 2018, 29 (07) : 954 - +
  • [10] Synthesis of difluoromethylenephosphonated oxindoles through visible-vight-induced radical cyclization of N-arylacrylamides
    Yin, Guojie
    Zhu, Mei
    Yang, Gangbin
    Wang, Xuemeng
    Fu, Weijun
    JOURNAL OF FLUORINE CHEMISTRY, 2016, 191 : 63 - 69