Metal-free cascade cyclization of alkenes toward perfluorinated oxindoles

被引:42
|
作者
Tang, Shi [1 ,3 ]
Li, Zhi-Hao [1 ]
Wang, Ming-Wei [1 ]
Li, Zhi-Ping [1 ]
Sheng, Rui-Long [2 ]
机构
[1] Jishou Univ, Coll Chem & Chem Engn, Jishou 416000, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
[3] Cent S Univ, Coll Chem & Chem Engn, Changsha 410083, Hunan, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
COPPER-CATALYZED TRIFLUOROMETHYLATION; N-ARYLACRYLAMIDES; RADICAL-ADDITION; CF3-CONTAINING OXINDOLES; ACTIVATED ALKENES; BOND FORMATION; PERFLUOROALKYLATION; IODIDES; FLUOROALKYLATION; CONSTRUCTION;
D O I
10.1039/c5ob00454c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple AIBN-mediated cyclization reaction of activated alkenes toward perfluorinated oxindoles is developed. In the presence of readily available AIBN, N-arylacrylamide and perfluoroalkyl iodides underwent perfluorination reaction to give perfluorinated oxindoles in good to excellent yields under metal-free conditions.
引用
收藏
页码:5285 / 5288
页数:4
相关论文
共 50 条
  • [31] Metal-Free, Organocatalytic Syn Diacetoxylation of Alkenes
    Zhong, Wenhe
    Liu, Shan
    Yang, Jun
    Meng, Xiangbao
    Li, Zhongjun
    ORGANIC LETTERS, 2012, 14 (13) : 3336 - 3339
  • [32] Metal-Free Cascade Methylation/Cyclization of N -Alkyl- N -methacryloylbenzamides with Dicumyl Peroxide
    Niu, Yan-Ning
    Xia, Xiao-Feng
    Yuan, Yuan
    SYNLETT, 2018, 29 (05) : 617 - 620
  • [33] Transition metal-free strategies for the stereoselective construction of spirocyclopropyl oxindoles
    Bacher, Emily P.
    Ashfeld, Brandon L.
    TETRAHEDRON, 2020, 76 (04)
  • [34] Metal-free polychloromethylation/cyclization of unactivated alkenes towards ring-fused tricyclic indolones and benzoimidazoles
    Wu, Yechun
    Liu, Han
    Liu, Lingli
    Yu, Jin-Tao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (35) : 7079 - 7084
  • [35] Metal-free radical cascade cyclization/haloazidation of enynones to access functionalized 1-indanones
    Yan, Hua-Feng
    Zou, Xiao
    Wang, Jian-Qiang
    Guo, Cheng
    Zuo, Hang-Dong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (05) : 1067 - 1072
  • [36] Convenient and Clean Synthesis of Isatins by Metal-Free Oxidation of Oxindoles
    Wei, Wen-Ting
    Ying, Wei-Wei
    Zhu, Wen-Ming
    Wu, Yi
    Huang, Yi-Ling
    Cao, Yi-Qi
    Wang, Yi-Ning
    Liang, Hongze
    SYNLETT, 2017, 28 (17) : 2307 - 2310
  • [37] Metal-Free Electrophilic Phosphination/Cyclization of Alkynes
    Unoh, Yuto
    Hirano, Koji
    Miura, Masahiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (17) : 6106 - 6109
  • [38] Metal-free trifluoroethylation of activated alkenes: rapid access to construct fluorinated 3,3-disubstituted 2-oxindoles
    Mai, Wen-Peng
    Sun, Bin
    Qian, Guan-Sheng
    Yuan, Jin-Wei
    Mao, Pu
    Yang, Liang-Ru
    Xiao, Yong-Mei
    TETRAHEDRON, 2015, 71 (44) : 8416 - 8423
  • [39] Metal-free photocatalytic trifluoromethylative pyridylation of unactivated alkenes
    He, Yu-Tao
    Kang, Dahye
    Kim, Inwon
    Hong, Sungwoo
    GREEN CHEMISTRY, 2018, 20 (22) : 5209 - 5214
  • [40] Metal-Free Oxyaminations of Alkenes Using Hydroxamic Acids
    Schmidt, Valerie A.
    Alexanian, Erik J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (30) : 11402 - 11405