Synthesis of 10H-indolo[1,2-a]indol-10-ones via palladium-catalyzed C-H bond activation and difluorocarbene transfer

被引:13
|
作者
Hu, Chengxian [1 ]
Mou, Dan [1 ]
Zhang, Xi [1 ]
Fu, Ying [1 ]
Huo, Congde [1 ]
Du, Zhengyin [1 ]
机构
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Key Lab Ecofunct Polymer Mat, Minist Educ, Lanzhou 730070, Peoples R China
基金
中国国家自然科学基金;
关键词
PEPTIDAL CHOLECYSTOKININ ANTAGONIST; ASPERGILLUS-ALLIACEUS; RECENT PROGRESS; INDOLONE; ANNULATION; ARYL; FERMENTATION; HETEROCYCLES; ASPERLICIN; MOLECULES;
D O I
10.1039/d2ob01493a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Pd-catalyzed annulation between 1-(2-iodophenyl)-1H-indoles and sodium difluorochloroacetate has been developed to synthesize 10H-indolo[1,2-a]indol-10-one derivatives via C-H bond activation and difluorocarbene transfer. Our route enables facile access to the targeted products with various substituents in moderate to high yields. This method features high reactivity, good functional group tolerance, a simple operation procedure, and mild reaction conditions. The reaction can be carried out on a gram scale.
引用
收藏
页码:8120 / 8124
页数:5
相关论文
共 50 条
  • [1] Base-Mediated N-Arylation for the Synthesis of 9H-Pyrrolo[1,2-a]indol-9-ones and 10H-Indolo[1,2-a]indol-10-ones
    Xu, Hongjin
    Sun, Li
    Song, Chuanjun
    HELVETICA CHIMICA ACTA, 2019, 102 (01)
  • [2] Synthesis of 10H-Indolo[1,2-a]indole Derivatives via Intramolecular Cycloaddition and H-Migration
    Zhao, Yulei
    Li, Shuai
    Fan, Yuhang
    Guo, Xuqiang
    Jiao, Xin
    Tian, Laijin
    Sun, Xuejun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (30) : 4358 - 4363
  • [3] Palladium-catalyzed C-H bond activation and decarboxylation for the assembly of indolo[1,2-f]phenanthridine
    Liu, Xiaobing
    Ban, Yong-Liang
    Liu, Yanjie
    Zhuang, Mengdie
    Zhou, Yao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (47) : 9188 - 9191
  • [4] Synthesis of C9,C10-Diheteroarylated Phenanthrenes via Palladium-Catalyzed C-H Bond Activation
    Bouzayani, Bilel
    Ben Salem, Ridha
    Soule, Jean-Francois
    Doucet, Henri
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (44) : 6092 - 6100
  • [5] Syntheses of indolo[1,2-a]quinazolinone derivatives via palladium catalyzed intramolecular C-H amidation
    Kotipalli, Trimurtulu
    Kavala, Veerababurao
    Janreddy, Donala
    Kuo, Chun-Wei
    Kuo, Ting-Shen
    Huang, Hsiu-Ni
    He, Chiu-Hui
    Yao, Ching-Fa
    RSC ADVANCES, 2014, 4 (05) : 2274 - 2283
  • [6] Palladium-Catalyzed Annulation via Acyl C-H Bond Activation
    Chen, Gui
    Yu, Yinghua
    Huang, Xueliang
    SYNLETT, 2018, 29 (16) : 2087 - 2092
  • [7] Palladium-Catalyzed Synthesis of Dihydrobenzoindolones via C-H Bond Activation and Alkyne Insertion
    Rodriguez, Jose F.
    Marchese, Austin D.
    Lautens, Mark
    ORGANIC LETTERS, 2018, 20 (14) : 4367 - 4370
  • [8] Regioselective C3 Alkenylation of 4H-pyrido[1,2-a] pyrimidin-4-ones via Palladium-Catalyzed C-H Activation
    Liu, Wenjie
    Wang, Shaohua
    Zhang, Qi
    Yu, Jingwen
    Li, Jiahe
    Xie, Zhiwei
    Cao, Hua
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (09) : 2436 - 2439
  • [9] Palladium-Catalyzed Direct Esterification via C-H Bond Activation of Aldehydes
    Yan, Xiao-Xiao
    Lu, Wen-Xiu
    Mao, Jian-Gang
    Xing, Jian
    Tang, Hong-Yu
    Huang, Shu-Yi
    Jiang, Wen
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13): : 9026 - 9036
  • [10] Functionalization of [60]Fullerene via Palladium-Catalyzed C-H Bond Activation
    Wang, Guan-Wu
    C-H BOND ACTIVATION AND CATALYTIC FUNCTIONALIZATION I, 2016, 55 : 119 - 136