Synthesis of Indoles by Conjugate Addition and Ligand-Free Copper-Catalyzed Intramolecular Arylation of Activated Acetylenes with o-Haloanilines

被引:27
|
作者
Gao, Detian [1 ]
Parvez, Masood [1 ]
Back, Thomas G. [1 ]
机构
[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
acetylenes; copper; cyclization; indoles; REACTION SEQUENCE; SULFONES; HETEROANNULATION; CYCLOADDITIONS; IODOANILINES; CYCLIZATIONS; DERIVATIVES; 1-ALKYNES; OXIDATION; PRODUCTS;
D O I
10.1002/chem.201002628
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Air and water welcome-ligands need not apply! A simple and efficient new synthesis of variously functionalized and substituted indoles was achieved by the addition and copper-catalyzed coupling of N-formyl-o-haloanilines with acetylenic sulfones, esters and ketones (see scheme; EWG=electron-withdrawing group). The reaction employs copper(II) acetate under ligand-free conditions without the need for exclusion of air and moisture. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:14281 / 14284
页数:4
相关论文
共 50 条
  • [41] Ligand free copper-catalyzed heterogeneous O-arylation reaction under green condition
    Maity, Tanmoy
    Saha, Debraj
    Das, Soma
    Bhunia, Susmita
    Koner, Subratanath
    CATALYSIS COMMUNICATIONS, 2015, 58 : 141 - 148
  • [42] Selective Copper-Catalyzed N-Arylation of Lactams with Arylboronic Acids under Base- and Ligand-Free Conditions
    Bathini, Thulasiram
    Rawat, Vikas Singh
    Sreedhar, Bojja
    SYNLETT, 2015, 26 (10) : 1348 - 1351
  • [43] Ligand-Free Copper-Catalyzed Regioselective C-2 Arylation of Imidazo[2,1-b]thiazoles
    Huang, Guoli
    Sun, Hongsheng
    Qiu, Xiaojie
    Jin, Can
    Lin, Chen
    Shen, Yingzhong
    Jiang, Juli
    Wang, Leyong
    ORGANIC LETTERS, 2011, 13 (19) : 5224 - 5227
  • [44] Ligand-Free Copper-Catalyzed N-Arylation of Pyrazolo[1,5-a]pyrimidin-7-Amines
    Pang, Ting
    Sang, Tian
    He, Jing
    Guo, Ruili
    Xie, Jianwei
    Liu, Ping
    APPLIED ORGANOMETALLIC CHEMISTRY, 2025, 39 (03)
  • [45] Copper-catalyzed enantioselective intramolecular conjugate addition/trapping reactions: Synthesis of cyclic compounds with multichiral centers
    Li, Kangying
    Alexakis, Alexandre
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (13) : 3765 - 3771
  • [46] Ligand-free Cu-catalyzed O-arylation of aliphatic diols
    Zheng, Yufen
    Zou, Wenxing
    Luo, Laichun
    Chen, Jiabei
    Lin, Songwen
    Sun, Qi
    RSC ADVANCES, 2015, 5 (81): : 66104 - 66108
  • [47] Ligand-Free Copper-Catalyzed Amination of Heteroaryl Halides with Alkyl- and Arylamines
    Liu, Zhen-Jiang
    Vors, Jean-Pierre
    Gesing, Ernst R. F.
    Bolm, Carsten
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3158 - 3162
  • [48] Copper-Catalyzed Ligand-Free Amidation of Benzylic Hydrocarbons and Inactive Aliphatic Alkanes
    Zeng, Hui-Ting
    Huang, Jing-Mei
    ORGANIC LETTERS, 2015, 17 (17) : 4276 - 4279
  • [49] Peptidic amidomonophosphane ligand for copper-catalyzed asymmetric conjugate addition of diorganozincs to cycloalkenones
    Soeta, Takahiro
    Selim, Khalid
    Kuriyama, Masami
    Tomioka, Kiyoshi
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (4-5) : 629 - 635
  • [50] Ligand-free synthesis of 2-aminoarylbenzoxazoles via copper-catalyzed C-N/C-O coupling
    Lu, Ju-You
    TETRAHEDRON LETTERS, 2020, 61 (51)