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
  • [21] Palladium-Catalyzed Trifluoromethylthiolation of Arenes via C-H Activation
    Xu Jiabin
    Chen Pinhong
    Ye Jinxing
    Liu Guosheng
    ACTA CHIMICA SINICA, 2015, 73 (12) : 1294 - 1297
  • [22] Palladium-Catalyzed Sonogashira-Coupling Conjoined C-H Activation: A Regioselective Tandem Strategy to Access Indolo- and Pyrrolo[1,2-a]quinolines
    Shukla, Satya Prakash
    Tiwari, Rakesh K.
    Verma, Akhilesh K.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 10382 - 10392
  • [23] Synthesis and reactions of 10,10-dimethyl-10H-pyrido[1,2-a]indol-6-ones
    Kappe, T
    Frühwirth, F
    Roschger, P
    Jocham, B
    Kremsner, J
    Stadlbauer, W
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (02) : 391 - 397
  • [24] Palladium-Catalyzed C-H Bond Acetoxylation via Electrochemical Oxidation
    Shrestha, Anuska
    Lee, Melissa
    Dunn, Anna L.
    Sanford, Melanie S.
    ORGANIC LETTERS, 2018, 20 (01) : 204 - 207
  • [25] Oxindole Synthesis via Palladium-catalyzed C-H Functionalization
    Magano, Javier
    Kiser, E. Jason
    Shine, Russell J.
    Chen, Michael H.
    Hughes, David
    ORGANIC SYNTHESES, 2013, 90 : 74 - +
  • [26] Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C-H and Dual C-H Bond Activation
    Wan, Jung-Chih
    Huang, Jun-Min
    Jhan, Yu-Huei
    Hsieh, Jen-Chieh
    ORGANIC LETTERS, 2013, 15 (11) : 2742 - 2745
  • [27] CARBOXYLATION OF ALKANES WITH CARBON-MONOXIDE VIA PALLADIUM-CATALYZED C-H BOND ACTIVATION
    TAKAKI, K
    NAKATA, K
    TANIGUCHI, Y
    FUJIWARA, Y
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1994, 52 (10) : 809 - 818
  • [28] Palladium-Catalyzed Oxirane-Opening Reaction with Arenes via C-H Bond Activation
    Wang, Zhen
    Kuninobu, Yoichiro
    Kanai, Motomu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (19) : 6140 - 6143
  • [29] Palladium-Catalyzed Regioselective Alkoxylation via C-H Bond Activation in the Dihydrobenzo[c]acridine Series
    Large, Benjamin
    Bourdreux, Flavien
    Damond, Aurelie
    Gaucher, Anne
    Prim, Damien
    CATALYSTS, 2018, 8 (04):
  • [30] Synthesis of isoindolinones via palladium-catalyzed C-H activation of N-methoxybenzamides
    Li, Dan-Dan
    Yuan, Ting-Ting
    Wang, Guan-Wu
    CHEMICAL COMMUNICATIONS, 2011, 47 (48) : 12789 - 12791