Metal-Free Synthesis of 3,3-Disubstituted Oxoindoles by Iodine(III)-Catalyzed Bromocarbocyclizations

被引:121
|
作者
Fabry, David C. [1 ]
Stodulski, Maciej [1 ]
Hoerner, Stefanie [1 ]
Gulder, Tanja [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
bromocarbocyclization; heterocycles; natural products; organocatalysis; oxoindoles; CATALYTIC ASYMMETRIC-SYNTHESIS; HYPERVALENT IODINE REAGENTS; ENANTIOSELECTIVE HALOCYCLIZATION; NUCLEOPHILIC ORGANOCATALYSTS; ELECTROPHILIC BROMINE; N-BROMOSUCCINIMIDE; ATOM ECONOMY; OXINDOLES; ALKENES; CHEMISTRY;
D O I
10.1002/chem.201201232
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:10834 / 10838
页数:5
相关论文
共 50 条
  • [1] Metal-Free Synthesis of Oxazolidine-2,4-diones and 3,3-Disubstituted Oxindoles via ICl-Induced Cyclization
    Yi, Wei
    Fang, Xing-Xiao
    Liu, Qing-Yun
    Liu, Gong-Qing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (47) : 6671 - 6681
  • [2] Synthesis of 3,3-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates
    Adhikari, Arijit A.
    Radal, Lea
    Chisholm, John D.
    SYNLETT, 2017, 28 (17) : 2335 - 2339
  • [3] Stereospecific synthesis of 3,3-disubstituted acrylonitriles by Heck reaction
    Masllorens, J
    Moreno-Mañas, M
    Pla-Quintana, A
    Pleixats, R
    Roglans, A
    SYNTHESIS-STUTTGART, 2002, (13): : 1903 - 1911
  • [4] Synthesis of 3,3-disubstituted oxetane building blocks
    Vigo, Daniele
    Stasi, Luigi
    Gagliardi, Stefania
    TETRAHEDRON LETTERS, 2011, 52 (05) : 565 - 567
  • [5] Palladium-Catalyzed Domino Heck/Phosphorylation towards 3,3-Disubstituted Phosphinonyloxindoles
    Lu, Guozhang
    Huangfu, Xinlei
    Wu, Zi'ang
    Tang, Guo
    Zhao, Yufen
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (21) : 4961 - 4965
  • [6] Metal-Free Coupling of 3-Alkenyl Oxoindoles by Nucleophilic Vinylic Substitution of Nitroolefins
    Zhang, Hongrui
    Liu, Yun
    Chen, Rui
    Xue, Jijun
    Li, Ying
    Tang, Yu
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (04) : 307 - 310
  • [7] Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles
    Li, Yuxiu
    Wang, Kuai
    Ping, Yuanyuan
    Wang, Yifan
    Kong, Wangqing
    ORGANIC LETTERS, 2018, 20 (04) : 921 - 924
  • [8] Metal-free iodine(III)-promoted synthesis of 2,5-diaryloxazoles
    Yang, Xueying
    Guo, Xin
    Qin, Mingda
    Yuan, Xinglong
    Jing, Huanwang
    Chen, Baohua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (17) : 3104 - 3108
  • [9] An Efficient Approach for 3,3-Disubstituted Oxindoles Synthesis: Aryl Iodine Catalyzed Intramolecular C-N Bond Oxidative Cross-Coupling
    Wang, Yang
    Yang, Mo
    Sun, Yuan-Yuan
    Wu, Zheng-Guang
    Dai, Hong
    Li, Shuhua
    ORGANIC LETTERS, 2021, 23 (22) : 8750 - 8754
  • [10] Divergent synthesis of 1,3,5-tri and 1,3-disubstituted pyrazoles under transition metal-free conditions
    Ma, Liyao
    Ou, Pengcheng
    Huang, Xueliang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (33) : 6487 - 6491