Palladium-Catalyzed Aryl Iodide Carbonylation as a Route to Imidazoline Synthesis: Design of a Five-Component Coupling Reaction

被引:39
|
作者
Bontemps, Sebastien [1 ,2 ]
Quesnel, Jeffrey S. [1 ,2 ]
Worrall, Kraig [1 ,2 ]
Arndtsen, Bruce A. [1 ,2 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
[2] Univ Toulouse, UPS, INPT, F-31077 Toulouse, France
基金
加拿大自然科学与工程研究理事会;
关键词
carbonylation; cyclizations; heterocycles; multicomponent reactions; palladium; AMINO-ACID DERIVATIVES; AMIDE BOND FORMATION; MULTICOMPONENT SYNTHESIS; CARBON-MONOXIDE; ENANTIOPURE IMIDAZOLINES; ATMOSPHERIC-PRESSURE; N-SULFONYLIMINES; VINYLIC HALIDES; BETA-LACTAMS; 2-IMIDAZOLINES;
D O I
10.1002/anie.201103885
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Take five: A new method employing aryl halide carbonylation to directly access heterocycles has been described (see scheme). In a single palladium-catalyzed reaction the catalyst mediates two consecutive carbonylation steps, thereby converting five components (aryl iodide, two units imine, and two units CO) into an imidazoline ring. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:8948 / 8951
页数:4
相关论文
共 50 条
  • [1] Palladium-catalyzed reductive carbonylation of aryl triflates with synthesis gas
    Brenrifuehrer, Anne
    Neumann, Helfried
    Beller, Matthias
    SYNLETT, 2007, (16) : 2537 - 2540
  • [2] Convenient synthesis of aryl ferrocenyl ketone via palladium-catalyzed carbonylation coupling
    Yang, Dong
    Liu, Zenglu
    Li, Ying
    Chen, Baohua
    SYNTHETIC COMMUNICATIONS, 2007, 37 (19-21) : 3759 - 3765
  • [3] Palladium-Catalyzed Carbonylation Reaction of Aryl Bromides with 2-Hydroxyacetophenones to Form Flavones
    Wu, Xiao-Feng
    Neumann, Helfried
    Beller, Matthias
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (40) : 12595 - 12598
  • [4] Synthesis of Acylphosphonates by a Palladium-Catalyzed Phosphonocarbonylation Reaction of Aryl Iodides with Phosphites
    Masuda, Yusuke
    Ishida, Naoki
    Murakami, Masahiro
    CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (02) : 321 - 324
  • [5] Palladium-catalyzed coupling reaction of alkenylgalliums with aryl halides
    Mikami, S
    Yorimitsu, H
    Oshima, K
    SYNLETT, 2002, (07) : 1137 - 1139
  • [6] Palladium-Catalyzed Defluorinative Coupling of Difluoroalkenes and Aryl Boronic Acids for Ketone Synthesis
    Sun, Guangwu
    Liu, Herui
    Wang, Xiu
    Zhang, Wenbo
    Miao, Wenjun
    Luo, Qinyu
    Gao, Bing
    Hu, Jinbo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (01)
  • [7] Palladium-catalyzed four-component difluoroalkylative carbonylation of aryl olefins and ethylene
    Bao, Zhi-Peng
    Zhang, Youcan
    Wu, Xiao-Feng
    JOURNAL OF CATALYSIS, 2022, 413 : 163 - 167
  • [8] Palladium-catalyzed carbonylation of thioacetates and aryl iodides for the synthesis of S-aryl thioesters
    Kim, Myungjin
    Yu, Subeen
    Kim, Jeung Gon
    Lee, Sunwoo
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (16): : 2447 - 2452
  • [9] Palladium-Catalyzed Carbonylation of Indoles for Synthesis of Indol-3-yl Aryl Ketones
    Zhao, Mi-Na
    Ran, Longfei
    Chen, Ming
    Ren, Zhi-Hui
    Wang, Yao-Yu
    Guan, Zheng-Hui
    ACS CATALYSIS, 2015, 5 (02): : 1210 - 1213
  • [10] Palladium-Catalyzed Four-Component Carbonylation Reactions of Acetylene: Synthesis of β-Perfluoroalkyl Acrylamides
    Cao, Zhusong
    Wang, Qiang
    Neumann, Helfried
    Beller, Matthias
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (47)