Rh(III)-Catalyzed Sequential C-H Amination/Annulation Cascade Reactions: Synthesis of Multisubstituted Benzimidazoles

被引:41
|
作者
Huang, Siqi [1 ]
Li, Huan [1 ]
Sun, Xiangying [2 ]
Xu, Linhua [1 ]
Wang, Lianhui [1 ]
Cui, Xiuling [1 ]
机构
[1] Huaqiao Univ, Sch Biomed Sci, Engn Res Ctr Mol Med,Minist Educ, Key Lab Fujian Mol Med,Key Lab Xiamen Marine & Ge, Xiamen 361021, Fujian, Peoples R China
[2] Huaqiao Univ, Sch Mat Sci, Xiamen 361021, Fujian, Peoples R China
关键词
N BOND FORMATION; RHODIUM(III)-CATALYZED SYNTHESIS; CATALYZED DIRECT; 4+2 ANNULATION; O BOND; ACTIVATION; ALKYNES; ACCESS; ANTHRANILS; FACILE;
D O I
10.1021/acs.orglett.9b01902
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and practical method to construct benzimidazoles via Rh(III)-catalyzed sequential C-H amination and annulation cascade reaction has been developed. The cascade reaction displays high step, atom, and redox economy, is compatible with the air, and has good functional group tolerance and high efficiency. The titled products can be easily further converted into imidazo[4,5-c]acridines, which were observed unique fluorescent properties.
引用
收藏
页码:5570 / 5574
页数:5
相关论文
共 50 条
  • [21] Ni-Catalyzed Dual C-H Annulation of Benzimidazoles with Alkynes for Synthesis of π-Extended Heteroarenes
    Qi, Shao-Long
    Li, Yue
    Li, Jiang-Fei
    Zhang, Tao
    Luan, Yu-Xin
    Ye, Mengchun
    ORGANIC LETTERS, 2021, 23 (10) : 4034 - 4039
  • [22] Intramolecular cascade annulation triggered by rhodium(III)-catalyzed sequential C(sp2) H activation and C(sp3)-H amination
    Song, Liangliang
    Tian, Guilong
    Van der Eycken, Johan
    Van der Eycken, Erik V.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 571 - 576
  • [23] Ruthenium(II)-Catalyzed Sequential C-H/N-H Alkene Annulation Cascade of Phenanthroimidazoles: Synthesis and Photophysical Studies
    Thakur, Rekha
    Paul, Kamaldeep
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (09): : 6016 - 6026
  • [24] Rh-Catalyzed aldehydic C-H alkynylation and annulation
    Rao, Maddali L. N.
    Ramakrishna, Boddu S.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (07) : 1402 - 1411
  • [25] Synthesis of indene-fused spiro-dibenz(ox)azepines via Rh(iii)-catalyzed cascade regioselective C-H activation/annulation
    Naskar, Koushik
    Karmakar, Sudip
    Mondal, Imtiaj
    Sarkar, Writhabrata
    Roy, Shantonu
    Roy, Anupam
    Deb, Indubhusan
    CHEMICAL COMMUNICATIONS, 2023, 59 (50) : 7751 - 7754
  • [26] Rh(iii)-catalyzed C-H annulation of sulfoxonium ylides with iodonium ylides towards isocoumarins
    Yin, Chuanliu
    Li, Lianghao
    Yu, Chuanming
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (05) : 1112 - 1116
  • [27] Rh(III)-Catalyzed Regioselective Functionalization of C-H Bonds of Naphthylcarbamates for Oxidative Annulation with Alkynes
    Zhang, Xuan
    Si, Weili
    Bao, Ming
    Asao, Naoki
    Yamamoto, Yoshinori
    Jin, Tienan
    ORGANIC LETTERS, 2014, 16 (18) : 4830 - 4833
  • [28] Ruthenium(II)-catalyzed C-H alkenylation/annulation cascade for the rapid synthesis of benzoimidazoisoindoles
    Selvaraju, Manikandan
    Wang, Ying-Lien
    Sun, Chung-Ming
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1358 - 1362
  • [29] Site-selective Cp* Rh(III)-catalyzed C-H amination of indolines with anthranils
    Mishra, Neeraj Kumar
    Jeon, Mijin
    Oh, Yongguk
    Jo, Hyeim
    Park, Jihye
    Han, Sangil
    Sharma, Satyasheel
    Han, Sang Hoon
    Jung, Young Hoon
    Kim, In Su
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (02): : 241 - 249
  • [30] Three-Component Synthesis of Isoquinolone Derivatives via Rh(III)-Catalyzed C-H Activation and Tandem Annulation
    Yang, Zhenke
    Liu, Jidan
    Li, Yuting
    Ding, Jiawen
    Zheng, Liyao
    Liu, Zhao-Qing
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21): : 14809 - 14818