Palladium-Catalyzed Domino C,N-Coupling/Carbonylation/Suzuki Coupling Reaction: An Efficient Synthesis of 2-Aroyl-/Heteroaroylindoles

被引：102
|
作者：
Arthuis, Martin
Pontikis, Renee [1 ]
Florent, Jean-Claude
机构：
[1] Ctr Rech, Inst Curie, F-75248 Paris 05, France
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 20期
关键词：
CARBONYLATION REACTIONS; DERIVATIVES; CYCLIZATION; CASCADE; INDOLE; REAGENT; AGENTS;
D O I：
10.1021/ol901875z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient one-pot synthesis of 2-aroylindoles using a domino palladium-catalyzed C,N-coupling/carbonylation/C,C-coupling sequence Is described. The reaction involved easily prepared 2-gem-dibromovinylanilines and boronic acids under carbon monoxide. Optimized reaction conditions allowed the construction of a wide variety of highly functionalized 2-aroyl-/heteroaroylindoles in satisfactory yields.
引用
收藏
页码：4608 / 4611
页数：4
相关论文
共 50 条
  • [21] A Mild Palladium-Catalyzed Suzuki Coupling Reaction of Quinoline Carboxylates with Boronic Acids
    Li, Wenjie
    Gao, Joe J.
    Zhang, Yongda
    Tang, Wenjun
    Lee, Heewon
    Fandrick, Keith R.
    Lu, Bruce
    Senanayake, Chris H.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (10) : 1671 - 1675
  • [22] Palladium-catalyzed cascade metallo-ene/Suzuki coupling reaction of allenamides
    Liang, Hanbing
    Yan, Fachao
    Dong, Xu
    Liu, Qing
    Wei, Xiaobing
    Liu, Sheng
    Dong, Yunhui
    Liu, Hui
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (21) : 3138 - 3141
  • [23] An efficient palladium-catalyzed coupling reaction for the preparation of biaryls and polyaryls
    Wang, ZY
    Zha, ZG
    Zhang, JH
    Wu, JH
    [J]. CHINESE CHEMICAL LETTERS, 2003, 14 (01) : 13 - 16
  • [24] An Efficient Ligandless Palladium-catalyzed Protocol for Suzuki-Miyaura Coupling Reaction of Potassium Aryltrifluoroborates in Water
    Liu, Leifang
    Li, Mingcheng
    Yang, Jianhua
    Zhu, Baoyong
    Wang, Xinfang
    [J]. CURRENT ORGANIC CHEMISTRY, 2018, 22 (20) : 2023 - 2028
  • [25] Efficient Pyrimidone-Promoted Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction
    Zhang, Hong-Ping
    Dai, You-Zhi
    Zhou, Xi
    Yu, Huang
    [J]. SYNLETT, 2012, (08) : 1221 - 1224
  • [26] Amide as an efficient ligand in the palladium-catalyzed Suzuki coupling reaction in water/ethanol under aerobic conditions
    Hai Yang Liu
    [J]. Chinese Chemical Letters, 2011, 22 (06) : 738 - 740
  • [27] Amide as an efficient ligand in the palladium-catalyzed Suzuki coupling reaction in water/ethanol under aerobic conditions
    Liu, Hai Yang
    Wang, Kun
    Fu, Hai Yan
    Yuan, Mao Lin
    Chen, Hua
    Li, Rui Xiang
    [J]. CHINESE CHEMICAL LETTERS, 2011, 22 (06) : 738 - 740
  • [28] Palladium-catalyzed enantioselective domino reaction for the efficient synthesis of vitamin E
    Tietze, LF
    Sommer, KM
    Zinngrebe, J
    Stecker, F
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (02) : 257 - 259
  • [29] Convenient synthesis of aryl ferrocenyl ketone via palladium-catalyzed carbonylation coupling
    Yang, Dong
    Liu, Zenglu
    Li, Ying
    Chen, Baohua
    [J]. SYNTHETIC COMMUNICATIONS, 2007, 37 (19-21) : 3759 - 3765
  • [30] ORGN 301-Synthesis of benzannulated N-heterocycles by a domino palladium-catalyzed C-C/C-N coupling
    Thansandote, Praew
    Rudolph, Alena
    Raemy, Manuel
    Lautens, Mark
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
12345