Rhodium(III)-catalyzed C-H activation and intermolecular annulation with terminal alkynes: from indoles to carbazoles

被引:77
作者
Jia, Jinlong [1 ,2 ]
Shi, Jingjing [1 ]
Zhou, Jie [1 ,3 ]
Liu, Xuelei [1 ]
Song, Yanling [2 ]
Xu, H. Eric [1 ,4 ]
Yi, Wei [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, VARI SIMM Ctr,Ctr Struct & Funct Drug Targets, Shanghai 201203, Peoples R China
[2] Shenyang Univ Chem Technol, Coll Pharmaceut & Biol Engn, Shenyang 110142, Peoples R China
[3] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China
[4] Van Andel Res Inst, Program Struct Biol & Drug Discovery, Lab Struct Sci, Grand Rapids, MI 49503 USA
关键词
N BOND FORMATION; EFFICIENT SYNTHESIS; ALKYNYLATION; FUNCTIONALIZATION; ARENES; RH; ALKENYLATION; ALKALOIDS; HYDROGENATION; HETEROCYCLES;
D O I
10.1039/c4cc09823d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein we disclose the first example of Rh(III)-catalyzed intermolecular annulation of indoles with terminal alkynes to give highly efficient one-pot access to privileged carbazoles. The mild reaction features moderate to good yields, exclusive regioselectivity, broad substrate scope, and excellent functional group tolerance.
引用
收藏
页码:2925 / 2928
页数:4
相关论文
共 50 条
  • [21] Rhodium(III)-Catalyzed Enantioselective Coupling of Indoles and 7-Azabenzonorbornadienes by C-H Activation/Desymmetrization
    Yang, Xifa
    Zheng, Guangfan
    Li, Xingwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (01) : 322 - 326
  • [22] Exploring a unique reactivity of N-heterocyclic carbenes (NHC) in rhodium(III)-catalyzed intermolecular C-H activation/annulation
    Ghorai, Debasish
    Choudhury, Joyanta
    CHEMICAL COMMUNICATIONS, 2014, 50 (96) : 15159 - 15162
  • [23] Rh(III)-Catalyzed [3+2] Annulation and C-H Alkenylation of Indoles with 1,3-Diynes by C-H Activation
    Kumar, Sanjeev
    Nunewar, Saiprasad
    Usama, Khan Mohammad
    Kanchupalli, Vinaykumar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (15) : 2223 - 2229
  • [24] Rhodium(III)-Catalyzed C-H Activation: Annulation of Petrochemical Feedstocks for the Construction of Isoquinolone Scaffolds
    Barber, Joyann S.
    Kong, Dehuan
    Li, Wei
    McAlpine, Indrawan J.
    Nair, Sajiv K.
    Sakata, Sylvie K.
    Sun, Nicole
    Patman, Ryan L.
    SYNLETT, 2021, 32 (02) : 202 - 206
  • [25] Rhodium(III)-Catalyzed Intermolecular Hydroarylation of Alkynes
    Schipper, Derek J.
    Hutchinson, Marieke
    Fagnou, Keith
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (20) : 6910 - +
  • [26] Rhodium(III)-Catalyzed Annulation of 2-Alkenyl Anilides with Alkynes through C-H Activation: Direct Access to 2-Substituted Indolines
    Font, Marc
    Cendon, Borja
    Seoane, Andres
    Luis Mascarenas, Jose
    Gulias, Moises
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (27) : 8255 - 8259
  • [27] Electrooxidative Rhodium(III)/Chiral Carboxylic Acid-Catalyzed Enantioselective C-H Annulation of Sulfoximines with Alkynes
    Zhou, Gang
    Zhou, Tao
    Jiang, Ao-Lian
    Qian, Pu-Fan
    Li, Jun-Yi
    Jiang, Bo-Yang
    Chen, Zi-Jia
    Shi, Bing-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (15)
  • [28] Rhodium(III)-catalyzed oxidative annulation of N-arylbenzamidines with maleimides via dual C-H activation
    Sankaram, G. Siva
    Sahoo, Tanmoy
    Sridhar, B.
    Reddy, B. V. Subba
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (08) : 1719 - 1724
  • [29] Rhodium(III)-Catalyzed Annulation of Azomethine Ylides with Alkynes via CH Activation
    Chen, Yuye
    Wang, Fen
    Zhen, Wencui
    Li, Xingwei
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (2-3) : 353 - 359
  • [30] Rhodium-catalyzed annulation of arenes with alkynes through weak chelation-assisted C-H activation
    Yang, Yudong
    Li, Kaizhi
    Cheng, Yangyang
    Wan, Danyang
    Li, Mingliang
    You, Jingsong
    CHEMICAL COMMUNICATIONS, 2016, 52 (14) : 2872 - 2884