Copper-Catalyzed Synthesis of N-Aryl and N-Sulfonyl Indoles from 2-Vinylanilines with O2 as Terminal Oxidant and TEMPO as Cocatalyst

被引：25
|
作者：
Liwosz, Timothy W. [1 ]
Chemler, Sherry R. [1 ]
机构：
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14620 USA
来源：
SYNLETT | 2015年 / 26卷 / 03期
基金：
美国国家卫生研究院;
关键词：
copper; oxidation; indoles; oxygen; TEMPO; C-H ACTIVATION; ONE-POT SYNTHESIS; 4-SUBSTITUTED INDOLES; AEROBIC OXIDATION; PALLADIUM; CYCLIZATION; BOND; ALCOHOLS; ANILINES; HETEROCYCLES;
D O I：
10.1055/s-0034-1379015
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper-catalyzed intramolecular alkene oxidative amination that utilizes TEMPO as cocatalyst and O-2 as the terminal oxidant has been developed. The method furnishes N-aryl and N-sulfonyl indoles from N-aryl and N-sulfonyl 2-vinylanilines, respectively. Additionally, sequential copper-catalyzed reactions where initial Chan-Lam coupling of 2-vinylanilines with arylboronic acids is followed by oxidative amination of the alkene can generate N-aryl indoles in one pot.
引用
收藏
页码：335 / 339
页数：5
相关论文
共 50 条
  • [31] Copper-catalyzed N-arylation of 2-arylindoles with aryl halides
    Liu, Wei
    Han, Li-Ya
    Liu, Rui-Li
    Xu, Li-Ge
    Bi, Yan-Lan
    CHINESE CHEMICAL LETTERS, 2014, 25 (09) : 1240 - 1243
  • [32] N-hetereocyclic carbene catalyzed synthesis of 2-aryl-Indoles
    Hovey, Michael
    Check, Christopher
    Sipher, Alexandra
    Scheidt, Karl
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [33] N-Heterocyclic-Carbene-Catalyzed Synthesis of 2-Aryl Indoles
    Hovey, M. Todd
    Check, Christopher T.
    Sipher, Alexandra F.
    Scheidt, Karl A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) : 9603 - 9607
  • [34] Copper-catalyzed N-arylation of 2-arylindoles with aryl halides
    Wei Liu
    Li-Ya Han
    Rui-Li Liu
    Li-Ge Xu
    Yan-Lan Bi
    Chinese Chemical Letters, 2014, 25 (09) : 1240 - 1243
  • [35] Copper-Catalyzed Synthesis of N-aryl-D-Glucosamines from Arylboronic Acids
    Tao, Chuanzhou
    Liu, Feng
    Xu, Bin
    Cao, Zhiling
    Wang, Huiyan
    Liu, Weiwei
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2013, 32 (07) : 411 - 423
  • [36] Synthesis of N-Aryl Amides by Ligand-Free Copper-Catalyzed ipso-Amidation of Arylboronic Acids with Nitriles
    Qiao, Yan
    Li, Gaoqiang
    Liu, Sha
    Yangkai, Yujie
    Tu, Jingxuan
    Xu, Feng
    SYNTHESIS-STUTTGART, 2017, 49 (08): : 1834 - 1838
  • [37] Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynes
    Jin, T
    Kamijo, S
    Yamamoto, Y
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (18) : 3789 - 3791
  • [38] Synthesis of 2-Aryl-2H-benzotrizoles from Azobenzenes and N-Sulfonyl Azides through Sequential Rhodium-Catalyzed Amidation and Oxidation in One Pot
    Ryu, Taekyu
    Min, Jiae
    Choi, Wonseok
    Jeon, Woo Hyung
    Lee, Phil Ho
    ORGANIC LETTERS, 2014, 16 (11) : 2810 - 2813
  • [39] Gold(I)-Catalyzed Rearrangement of N-Aryl 2-Alkynylazetidines to Pyrrolo[1,2-a]indoles
    Kern, Nicolas
    Hoffmann, Marie
    Blanc, Aurelien
    Weibel, Jean-Marc
    Pale, Patrick
    ORGANIC LETTERS, 2013, 15 (04) : 836 - 839
  • [40] Gold-Catalyzed Hydroarylation of N-Aryl Alkynamides for the Synthesis of 2-Quinolinones
    Vacala, Taylor
    Bejcek, Lauren P.
    Williams, Chloe G.
    Williamson, Alexandra C.
    Vadola, Paul A.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (05): : 2558 - 2569
12345