Electrochemical C-H/N-H Functionalization for the Synthesis of Highly Functionalized (Aza)indoles

被引：209
|
作者：
Hou, Zhong-Wei [1 ,2 ]
Mao, Zhong-Yi [1 ,2 ]
Zhao, Huai-Bo [1 ,2 ]
Melcamu, Yared Yohannes [1 ,2 ]
Lu, Xin [1 ,2 ]
Song, Jinshuai [1 ,2 ,3 ]
Xu, Hai-Chao [1 ,2 ]
机构：
[1] Xiamen Univ, Collaborat Innovat Ctr Chem Energy Mat, State Key Lab Phys Chem Solid Surfaces, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China
[2] Xiamen Univ, Dept Chem, Xiamen, Peoples R China
[3] Chinese Acad Sci, Fujian Inst Res Struct Matter, Fuzhou 350002, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 32期
关键词：
electrochemistry; heterocycles; indoles; radicals; redox chemistry; COUPLED ELECTRON-TRANSFER; INTERNAL ALKYNES; ORGANIC ELECTROSYNTHESIS; COMPLEX-MOLECULES; INDOLE SYNTHESIS; AMIDYL RADICALS; GENERATION; ANNULATION; OXIDATION; ANILINES;
D O I：
10.1002/anie.201602616
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Indoles and azaindoles are among the most important heterocycles because of their prevalence in nature and their broad utility in pharmaceutical industry. Reported herein is an unprecedented noble-metal-and oxidant-free electrochemical method for the coupling of (hetero)arylamines with tethered alkynes to synthesize highly functionalized indoles, as well as the more challenging azaindoles.
引用
收藏
页码：9168 / 9172
页数：5
相关论文
共 50 条
  • [1] Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles
    Kim, Youyoung
    Kim, Dongwook
    Chang, Sukbok
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (92) : 12309 - 12312
  • [2] Iron-catalyzed intramolecular C-H amination for the synthesis of N-H carbazoles and indoles
    Wang, Zheng-Lin
    Zhang, Yun-Hao
    Huang, Jun-Yu
    Zhou, Jian
    Yu, Ya-Qin
    Feng, Dexin
    Xu, Da-Zhen
    [J]. GREEN CHEMISTRY, 2023, 25 (11) : 4463 - 4468
  • [3] N-H and C-H Functionalization of Sulfoximine: Recent Advancement and Prospects
    Ghosh, Prasanjit
    Ganguly, Bhaskar
    Das, Sajal
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (12) : 2035 - 2082
  • [4] Asymmetric C-H and N-H Functionalization of Indoles Involving Central Chirality via Chiral Phosphoric Acid Catalysis
    Gashaw, Alemayehu
    Debeli, Dereje Kebebew
    Chemeda, Meseret
    [J]. MINI-REVIEWS IN ORGANIC CHEMISTRY, 2022, 19 (05) : 654 - 674
  • [5] Electrochemical intramolecular C-H/N-H functionalization for the synthesis of isoxazolidine-fused isoquinolin-1(2H)-ones
    Zhang, Lin-Bao
    Geng, Rui-Sen
    Wang, Zi-Chen
    Ren, Guang-Yi
    Wen, Li-Rong
    Li, Ming
    [J]. GREEN CHEMISTRY, 2020, 22 (01) : 16 - 21
  • [6] Palladium(II)-Catalyzed Tandem Cyclization/C-H Functionalization of Alkynes for the Synthesis of Functionalized Indoles
    Xia, Xiao-Feng
    Wang, Ning
    Zhang, Lu-Lu
    Song, Xian-Rong
    Liu, Xue-Yuan
    Liang, Yong-Min
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20): : 9163 - 9170
  • [7] Rhodium(III)-Catalyzed C-H/N-H Functionalization with Hydrogen Evolution
    Xie, Hui
    Jiang, Jijun
    Wang, Jun
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (33) : 7365 - 7368
  • [8] Progress and perspectives of electrochemical insights for C-H and N-H sulfonylation
    Jamshidi, Mahdi
    Amani, Ameneh
    Khazalpour, Sadegh
    Torabi, Sara
    Nematollahi, Davood
    [J]. NEW JOURNAL OF CHEMISTRY, 2021, 45 (39) : 18246 - 18267
  • [9] Selective Synthesis of Isoquinolines by Rhodium(III)-Catalyzed C-H/N-H Functionalization with α-Substituted Ketones
    Li, Jie
    Zhang, Zhao
    Tang, Mengyao
    Zhang, Xiaolei
    Jin, Jian
    [J]. ORGANIC LETTERS, 2016, 18 (15) : 3898 - 3901
  • [10] Nickel-catalyzed alkyne annulation by anilines: versatile indole synthesis by C-H/N-H functionalization
    Song, Weifeng
    Ackermann, Lutz
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (59) : 6638 - 6640
12345