General and Efficient Synthesis of Indoles through Triazene-Directed C-H Annulation

被引：211
|
作者：
Wang, Chengming [1 ]
Sun, Huan [1 ]
Fang, Yan [1 ]
Huang, Yong [1 ]
机构：
[1] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Key Lab Chem Genom, Shenzhen, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 22期
关键词：
C-H activation; indole; N-N cleavage; rhodium; triazene; N-ARYL ENAMINES; BOND FORMATION; 2,3-DISUBSTITUTED INDOLES; STEREOSELECTIVE-SYNTHESIS; OXIDATIVE CYCLIZATION; CATALYZED ANNULATION; O BOND; ACTIVATION; FUNCTIONALIZATION; ALKALOIDS;
D O I：
10.1002/anie.201301742
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Unprotected indoles are prepared with the title method, which has a wide scope for alkynes. Excellent regioselectivity was accomplished for aryl-alkyl and alkyl-alkyl disubstituted acetylenes. This reaction features an unusual 1,2 rhodium migration and ring-contraction-triggered N-N bond cleavage. It allows rapid conversion of the reaction products into several functional molecules. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：5795 / 5798
页数：4
相关论文
共 50 条
  • [1] Synthesis of Indolo[2,1-a]isoquinolines via a Triazene-Directed C-H Annulation Cascade
    Sun, Huan
    Wang, Chengming
    Yang, Yun-Fang
    Chen, Ping
    Wu, Yun-Dong
    Zhang, Xinhao
    Huang, Yong
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (24): : 11863 - 11872
  • [2] Enantioselective C-H Annulation of Indoles with Diazo Compounds through a Chiral Rh(III) Catalyst
    Chen, Xiaohong
    Yang, Shujing
    Li, Helong
    Wang, Bo
    Song, Guoyong
    ACS CATALYSIS, 2017, 7 (04): : 2392 - 2396
  • [3] Synthesis of indoles and polycyclic amides via ruthenium(II)-catalyzed C-H activation and annulation
    Lin, Hui
    Li, Shuai-Shuai
    Dong, Lin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) : 11228 - 11234
  • [4] Organoselenium-catalyzed synthesis of indoles through intramolecular C-H amination
    Zhang, Xuelin
    Guo, Ruizhi
    Zhao, Xiaodan
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10): : 1334 - 1337
  • [5] Free Amine, Hydroxyl and Sulfhydryl Directed C-H Functionalization and Annulation: Application to Heterocycle Synthesis
    Kumar, Sandeep
    Kumar, Akshay
    Sharma, Dharminder
    Das, Pralay
    CHEMICAL RECORD, 2022, 22 (02):
  • [6] Annulation of aromatic Imines via directed C-H bond activation
    Thalji, RK
    Ahrendt, KA
    Bergman, RG
    Ellman, JA
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17): : 6775 - 6781
  • [7] Electrooxidative Annulation of Unsaturated Molecules via Directed C-H Activation
    Xie Wucheng
    Chen Xu
    Li Yunyue
    Lin Jieling
    Chen Wanwen
    Shi Junjun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (05) : 1286 - 1306
  • [8] Transformation of C-H bonds through a bidentate directed C-H activation
    Chatani, Naoto
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [9] Copper-catalyzed intramolecular annulation through C-H activation: Synthesis of carbazolones
    Bashkar, Mohammad
    Nowrouzi, Najmeh
    Mohammadizadeh, Mohammad Reza
    APPLIED ORGANOMETALLIC CHEMISTRY, 2023, 37 (07)
  • [10] Atroposelective isoquinolinone synthesis through cobalt-catalysed C-H activation and annulation
    Si, Xiao-Ju
    Yang, Dandan
    Sun, Meng-Chan
    Wei, Donghui
    Song, Mao-Ping
    Niu, Jun-Long
    NATURE SYNTHESIS, 2022, 1 (09): : 709 - 718
12345