Effect of water on the palladium-catalyzed amidation of aryl bromides

被引:47
|
作者
Dallas, AS
Gothelf, KV
机构
[1] Aarhus Univ, Dept Chem, Interdisciplinary Nanosci Ctr, DK-8000 Aarhus, Denmark
[2] Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus, Denmark
来源
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 08期
关键词
D O I
10.1021/jo0500176
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The presence of water was found to have a significant impact on the conversion of some Hartwig-Buchwald reactions between amides with arylbromides. Seven amidation reactions were studied in a series of experiments containing 0-400 mol % water. When cesium carbonate is used as the base both in dioxane and toluene, water can have a beneficial effect. The experiments have also shown that for some reactions, anhydrous conditions are unnecessary and sometimes can hinder the reaction.
引用
收藏
页码:3321 / 3323
页数:3
相关论文
共 50 条
  • [1] Intramolecular palladium-catalyzed aryl amination and aryl amidation
    Wolfe, JP
    Rennels, RA
    Buchwald, SL
    TETRAHEDRON, 1996, 52 (21) : 7525 - 7546
  • [2] Palladium-catalyzed α-arylation of aldehydes with aryl bromides
    Terao, Y
    Fukuoka, Y
    Satoh, T
    Miura, M
    Nomura, M
    TETRAHEDRON LETTERS, 2002, 43 (01) : 101 - 104
  • [3] Mechanistic investigation of palladium-catalyzed amidation of aryl halides
    Liang, Yun
    Ren, Ying
    Jia, Jianfeng
    Wu, Hai-Shun
    JOURNAL OF MOLECULAR MODELING, 2016, 22 (03) : 1 - 12
  • [4] PALLADIUM-CATALYZED AMIDATION OF ARYL, HETEROCYCLIC, AND VINYLIC HALIDES
    SCHOENBE.A
    HECK, RF
    JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (23): : 3327 - 3331
  • [5] Mechanistic investigation of palladium-catalyzed amidation of aryl halides
    Yun Liang
    Ying Ren
    Jianfeng Jia
    Hai-Shun Wu
    Journal of Molecular Modeling, 2016, 22
  • [6] Palladium-Catalyzed Thiocarbonylation of Aryl, Vinyl, and Benzyl Bromides
    Burhardt, Mia N.
    Ahlburg, Andreas
    Skrydstrup, Troels
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (24): : 11830 - 11840
  • [7] Palladium-catalyzed direct arylation of thiazoles with aryl bromides
    Yokooji, A
    Okazawa, T
    Satoh, T
    Miura, M
    Nomura, M
    TETRAHEDRON, 2003, 59 (30) : 5685 - 5689
  • [8] Versatile palladium-catalyzed double carbonylation of aryl bromides
    Shen, Chaoren
    Fink, Cornel
    Laurenczy, Gabor
    Dyson, Paul J.
    Wu, Xiao-Feng
    CHEMICAL COMMUNICATIONS, 2017, 53 (92) : 12422 - 12425
  • [9] Palladium-Catalyzed Germylation of Aryl Bromides and Aryl Triflates Using Hexamethyldigermane
    Komami, Narumi
    Matsuoka, Keitaro
    Yoshino, Tatsuhiko
    Matsunaga, Shigeki
    SYNTHESIS-STUTTGART, 2018, 50 (10): : 2067 - 2075
  • [10] Synthesis of Amides via Palladium-Catalyzed Amidation of Aryl Halides
    Jiang, Huanfeng
    Liu, Bifu
    Li, Yibiao
    Wang, Azhong
    Huang, Huawen
    ORGANIC LETTERS, 2011, 13 (05) : 1028 - 1031