Regioselective hydroarylation and arylation of maleimides with indazoles via a Rh(iii)-catalyzed C-H activation

被引：34
|
作者：
Ghosh, Asim Kumar [1 ]
Samanta, Sadhanendu [1 ]
Ghosh, Payel [1 ]
Neogi, Sukanya [1 ]
Hajra, Alakananda [1 ]
机构：
[1] Visva Rharati Cent Univ, Dept Chem, Santini Ketan 731235, W Bengal, India
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 16期
关键词：
SUBSTITUTED MALEIMIDE; AROMATIC AMIDES; ALKYLATION; ALKENYLATION; BONDS; (HETERO)ARENES; DERIVATIVES; ALDEHYDES; DESIGN; CANCER;
D O I：
10.1039/d0ob00353k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Switchable Rh(iii)-catalyzed highly regioselective hydroarylation and oxidative arylation of maleimides with 2-arylindazoles via C-H activation have been demonstrated. The reaction affords 3-(2-(2H-indazol-2-yl)phenyl)succinimide and 3-(2-(2H-indazol-2-yl)phenyl)maleimide derivatives in high yields with wide functional group tolerance. A mechanistic study was performed to depict C-H bond cleavage that might be involved in the turnover limiting step.
引用
收藏
页码：3093 / 3097
页数：5
相关论文
共 50 条
  • [31] Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C-H activation
    Semakul N.
    Jackson K.E.
    Paton R.S.
    Rovis T.
    Paton, Robert S. (robert.paton@chem.ox.ac.uk), 1600, Royal Society of Chemistry (08): : 1015 - 1020
  • [32] Direct synthesis of indazole derivatives via Rh(iii)-catalyzed C-H activation of phthalazinones and allenes
    Yin, Chuanliu
    Zhong, Tianshuo
    Zheng, Xiangyun
    Li, Lianghao
    Zhou, Jian
    Yu, Chuanming
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (35) : 7701 - 7705
  • [33] Construction of Peptide-Isoquinolone Conjugates via Rh(III)- Catalyzed C-H Activation/Annulation
    Song, Liangliang
    Lv, Zhenwei
    Li, Yan
    Zhang, Kui
    Van der Eycken, Erik V.
    Cai, Lingchao
    ORGANIC LETTERS, 2023, 25 (17) : 2996 - 3000
  • [34] Rh(III)-Catalyzed Cascade Oxidative Olefination/Cyclization of Picolinamides and Alkenes via C-H Activation
    Cai, Shangun
    Chen, Chao
    Shao, Peng
    Xi, Chanjuan
    ORGANIC LETTERS, 2014, 16 (11) : 3142 - 3145
  • [35] Rapid Synthesis of Alkenylated BINOL Derivatives via Rh(III)-Catalyzed C-H Bond Activation
    Liu, Hao
    Luo, Yi
    Zhang, Jing
    Liu, Man
    Dong, Lin
    ORGANIC LETTERS, 2020, 22 (12) : 4648 - 4652
  • [36] Rh(III)-Catalyzed Chemodivergent Coupling of N-Phenoxyacetamides and Alkylidenecyclopropanes via C-H Activation
    Xu, Guiqing
    Chen, Qi
    Wu, Fen
    Bai, Dachang
    Chang, Junbiao
    Li, Xingwei
    ORGANIC LETTERS, 2021, 23 (08) : 2927 - 2932
  • [37] ORGN 890-Rh(I)-Catalyzed alkylation and arylation of quinolines and pyridines via C-H bond activation
    Lewis, Jared C.
    Bergman, Robert G.
    Ellman, Jonathan A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [38] Rh(III)-Catalyzed Synthesis of Isocoumarins via C-H Activation of Phenacyl Phosphoniums with Iodonium Ylides
    Jiang, Lu
    Gao, Lei
    Li, Xiaofei
    Shao, Tingting
    Yao, Jinzhong
    Miao, Maozhong
    Zhou, Hongwei
    SYNTHESIS-STUTTGART, 2024, 56 (01): : 47 - 54
  • [39] Rh(III)-Catalyzed intramolecular redox-neutral cyclization of alkenes via C-H activation
    Shi, Zhuangzhi
    Boultadakis-Arapinis, Melissa
    Koester, Dennis C.
    Glorius, Frank
    CHEMICAL COMMUNICATIONS, 2014, 50 (20) : 2650 - 2652
  • [40] Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenes via Rh(III)-catalyzed C-H activation
    Semakul, Natthawat
    Jackson, Kelvin E.
    Paton, Robert S.
    Rovis, Tomislav
    CHEMICAL SCIENCE, 2017, 8 (02) : 1015 - 1020
12345