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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 38期
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
  • [21] AN EFFICIENT SYNTHESIS OF ARYL ESTERS BY PALLADIUM-CATALYZED CARBONYLATION OF 4-BROMOBIPHENYL
    KUBOTA, Y
    HANAOKA, TA
    TAKEUCHI, K
    SUGI, Y
    SYNLETT, 1994, (07) : 515 - 517
  • [22] Palladium-catalyzed three-component coupling reaction of aryl halides, norbornadiene and alkynols. Convenient synthesis for their ternary coupling products
    Choi, CK
    Tomita, I
    Endo, T
    CHEMISTRY LETTERS, 1999, (11) : 1253 - 1254
  • [23] 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
  • [24] Multicomponent Reaction: Palladium-Catalyzed Carbonylation of Aryl Halides and Alkyl Halides to Aromatic Esters
    Zhu, Fengxiang
    Yin, Pengpeng
    Zhang, Pengbo
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 88 (08): : 5153 - 5160
  • [25] Palladium-catalyzed cross-carbonylation of aryl iodides with five-membered cyclic olefins
    Satoh, Tetsuya
    Itaya, Tomoaki
    Okuro, Kazumi
    Miura, Masahiro
    Nomura, Masakatsu
    Journal of Organic Chemistry, 1995, 60 (22):
  • [26] Palladium-catalyzed cross-coupling reaction of silicone with aryl chlorides
    Koike, T
    Mori, A
    SYNLETT, 2003, (12) : 1850 - 1852
  • [27] Palladium-Catalyzed Cross-Coupling Reaction of Alkyltrifluorosilanes with Aryl Halides
    Matsuhashi, H.
    Asai, S.
    Hirabayashi, K.
    Hatanaka, Y.
    Bulletin of the Chemical Society of Japan, 70 (02):
  • [28] A new reaction sequence involving palladium-catalyzed unsymmetrical aryl coupling
    Faccini, F
    Motti, E
    Catellani, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (01) : 78 - 79
  • [29] Palladium-catalyzed cross-coupling reaction of alkyltrifluorosilanes with aryl halides
    Matsuhashi, H
    Asai, S
    Hirabayashi, K
    Mori, A
    Hiyama, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (02) : 437 - 444
  • [30] A palladium-catalyzed coupling reaction of aryl nonaflates, sulfur dioxide, and hydrazines
    An, Yuanyuan
    Xia, Hongguang
    Wu, Jie
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (05) : 1665 - 1669
12345