Formal [4+2] Reaction between 1,3-Diynes and Pyrroles: Gold(I)-Catalyzed Indole Synthesis by Double Hydroarylation

被引：82
|
作者：
Matsuda, Yuka [1 ]
Naoe, Saori [1 ]
Oishi, Shinya [1 ]
Fujii, Nobutaka [1 ]
Ohno, Hiroaki [1 ]
机构：
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 04期
基金：
日本学术振兴会;
关键词：
carbazoles; cascade reaction; gold catalysis; hydroarylation; indoles; HOMOGENEOUS GOLD CATALYSIS; ONE-POT SYNTHESIS; POLYCYCLIC COMPOUNDS; HYDROAMINATION; CONSTRUCTION; CASCADE; ALKYNES; CYCLIZATION; INHIBITORS; ALKALOIDS;
D O I：
10.1002/chem.201405903
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Indole synthesis by a gold(I)-catalyzed intermolecular formal [4+2] reaction between 1,3-diynes and pyrroles has been developed. This reaction involves the hydroarylation of 1,3-diynes with pyrroles followed by an intramolecular hydroarylation to give the 4,7-disubstituted indoles. This reaction can also be applied to the synthesis of carbazoles when indoles are used as the nucleophiles instead of pyrroles.
引用
收藏
页码：1463 / 1467
页数：5
相关论文
共 50 条
  • [1] Gold-Catalyzed Homocoupling Reaction of Terminal Alkynes to 1,3-Diynes
    Zhu, Mei
    Ning, Ma
    Fu, Weijun
    Xu, Chen
    Zou, Guanglong
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (04): : 1325 - 1328
  • [2] Cobalt(III)-Catalyzed Chemo- and Regioselective [4+2]-Annulation of Aromatic Sulfoxonium Ylides with 1,3-Diynes
    Yadav, Suresh Kumar
    Ramesh, Balu
    Jeganmohan, Masilamani
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (06) : 4134 - 4153
  • [3] Ru(II)-Catalyzed Regioselective Redox-Neutral [4+2] Annulation of N-Chlorobenzamides with 1,3-Diynes at Room Temperature for the Synthesis of Isoquinolones
    Ghosh, Arijit
    Sapkal, Goraksha T.
    Pawar, Amit B.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (07) : 4704 - 4719
  • [4] Cobalt(I)-catalyzed [4π+2π] cycloaddition reactions of 1,3-diynes with 1,3,5-cyclooctatriene
    D'yakonov, Vladimir A.
    Kadikova, Gulnara N.
    Nasretdinov, Ramil N.
    Dzhemilev, Usein M.
    TETRAHEDRON LETTERS, 2017, 58 (19) : 1839 - 1841
  • [5] Access to 2,5-Diamidopyrroles and 2,5-Diamidofurans by Au(I)-Catalyzed Double Hydroamination or Hydration of 1,3-Diynes
    Kramer, Soren
    Madsen, Julie L. H.
    Rottlander, Mario
    Skrydstrup, Troels
    ORGANIC LETTERS, 2010, 12 (12) : 2758 - 2761
  • [6] Traceless Bidentate Directing Group Assisted Cobalt-Catalyzed sp2-C-H Activation and [4+2]-Annulation Reaction with 1,3-Diynes
    Dey, Arnab
    Volla, Chandra M. R.
    ORGANIC LETTERS, 2020, 22 (19) : 7480 - 7485
  • [7] Gold(I)-Catalyzed Generation of the Two Components of a Formal [4+2] Cycloaddition Reaction for the Synthesis of Tetracyclic Pyrano[2,3,4-de]chromenes
    Arto, Tamara
    Fananas, Francisco J.
    Rodriguez, Felix
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (25) : 7218 - 7221
  • [8] Gold(I)-Catalyzed and Ligand-Controlled Regioselective Cascade Cycloisomerizations of Bis(indolyl)-1,3-diynes and a Mechanistic Explanation
    Zhang, Yan-Yan
    Wei, Yin
    Shi, Min
    ORGANIC LETTERS, 2019, 21 (19) : 7799 - 7803
  • [9] Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives
    Moran-Poladura, Pablo
    Rubio, Eduardo
    Gonzalez, Jose M.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2120 - 2128
  • [10] Transition-Metal-Catalyzed Synthesis of 1,3-Diynes and Ynamides from 2-Bromo-1-iodoalkenes
    Xue, Jun
    Luo, Miao-Ting
    Wen, Yue-Lu
    Ye, Min
    Liu, Liang-Xian
    Chen, Zheng-Wang
    SYNTHESIS-STUTTGART, 2014, 46 (23): : 3191 - 3198
12345