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
  • [41] Synthesis of ferrocene amides and α-ketoamides via palladium-catalyzed homogeneous carbonylation reaction
    Szarka, Z
    Skoda-Földes, R
    Kuik, A
    Berente, Z
    Kollár, L
    SYNTHESIS-STUTTGART, 2003, (04): : 545 - 550
  • [42] Palladium-catalyzed synthesis of aryl ketones by coupling of aryl bromides with an acyl anion equivalent
    Takemiya, Akihiro
    Hartwig, John F.
    Journal of the American Chemical Society, 2006, 128 (46): : 14800 - 14801
  • [43] Palladium-catalyzed synthesis of aryl ketones by coupling of aryl bromides with an acyl anion equivalent
    Takemiya, Akihiro
    Hartwig, John F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) : 14800 - 14801
  • [44] Optimization of a palladium-catalyzed multi-component coupling reaction for the synthesis of a, a-unsaturated-a-lactones
    Malinakova, HC
    Hopkins, CD
    Guan, L
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U408 - U408
  • [45] Synthesis of Indoles through Palladium-Catalyzed Three-Component Reaction of Aryl Iodides, Alkynes, and Diaziridinone
    Zhou, Bo
    Wu, Zhuo
    Ma, Ding
    Ji, Xiaoming
    Zhang, Yanghui
    ORGANIC LETTERS, 2018, 20 (20) : 6440 - 6443
  • [46] 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)
  • [47] Palladium-catalyzed cross-coupling reaction of potassium diaryldifluoroborates with aryl halides
    Ito, T
    Iwai, T
    Mizuno, T
    Ishino, Y
    SYNLETT, 2003, (10) : 1435 - 1438
  • [48] PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF FUNCTIONALIZED ALKYLTRIFLUOROSILANES WITH ARYL HALIDES
    MATSUHASHI, H
    KUROBOSHI, M
    HATANAKA, Y
    HIYAMA, T
    TETRAHEDRON LETTERS, 1994, 35 (35) : 6507 - 6510
  • [49] Palladium-catalyzed cross-coupling reaction of cyclopropylboronic acids with aryl triflates
    Yao, ML
    Deng, MZ
    SYNTHESIS-STUTTGART, 2000, (08): : 1095 - 1100
  • [50] Palladium-catalyzed cross-coupling reaction of aryl trimethoxysilanes with terminal alkynes
    Ye, Zhishi
    Liu, Miaochang
    Lin, Baoda
    Wu, Huayue
    Ding, Jinchang
    Cheng, Jiang
    TETRAHEDRON LETTERS, 2009, 50 (05) : 530 - 532