Palladium-catalyzed Suzuki cross-coupling of aryl halides with aryl boronic acids in the presence of glucosamine-based phosphines

被引：23
|
作者：
Kolodziuk, R
Penciu, A
Tollabi, M
Framery, E
Goux-Henry, C
Iourtchenko, A
Sinou, D
机构：
[1] Univ Lyon 1, CPE Lyon, Lab Synthese Asymetr, CNRS, F-69622 Villeurbanne, France
[2] Natl Acad Sci Ukraine, Inst Organ Chem, UA-02094 Kiev, Ukraine
来源：
JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2003年 / 687卷 / 02期
关键词：
Suzuki coupling; phosphine; carbohydrate; water-soluble;
D O I：
10.1016/S0022-328X(03)00636-3
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Carbohydrate-substituted phosphines are easily obtained in quite good yields by coupling of protected or non-protected D-glucosamine with the corresponding diphenylphosphino acid. These neutral ligands, in association with palladium acetate, are very active catalysts in the Suzuki cross-coupling reaction. The polyhydroxy phosphines are more active than the peracetylated phosphines. The process tolerates electron-rich as well as electron-poor substituents. Excellent turnovers, up to 97 000 are observed. (C) 2003 Elsevier Science B.V. All rights reserved.
引用
收藏
页码：384 / 391
页数：8
相关论文
共 50 条
  • [41] Mechanism of palladium-catalyzed decarboxylative cross-coupling between cyanoacetate salts and aryl halides
    JIANG YuanYe FU Yao LIU Lei Department of Chemistry University of Science and Technology of China Hefei China Department of Chemistry Tsinghua University Beijing China
    Science China(Chemistry), 2012, 55 (10) : 2057 - 2062
  • [42] Mechanism of palladium-catalyzed decarboxylative cross-coupling between cyanoacetate salts and aryl halides
    YuanYe Jiang
    Yao Fu
    Lei Liu
    Science China Chemistry, 2012, 55 : 2057 - 2062
  • [43] Palladium-Catalyzed Negishi Cross-Coupling Reaction of Aryl Halides with (Difluoromethyl)zinc Reagent
    Aikawa, Kohsuke
    Serizawa, Hiroki
    Ishii, Koki
    Mikami, Koichi
    ORGANIC LETTERS, 2016, 18 (15) : 3690 - 3693
  • [44] Palladium-catalyzed homocoupling and cross-coupling reactions of Aryl halides in poly(ethylene glycol)
    Wang, LA
    Zhang, YH
    Liu, LF
    Wang, YG
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03): : 1284 - 1287
  • [45] Arylation of α-Chiral Ketones by Palladium-Catalyzed Cross-Coupling Reactions of Tosylhydrazones with Aryl Halides
    Barluenga, Jose
    Escribano, Maria
    Aznar, Fernando
    Valdes, Carlos
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (38) : 6856 - 6859
  • [46] Palladium-catalyzed cross-coupling reactions of 2-indolyldimethylsilanois with substituted aryl halides
    Denmark, SE
    Baird, JD
    ORGANIC LETTERS, 2004, 6 (20) : 3649 - 3652
  • [47] A mild and versatile method for palladium-catalyzed cross-coupling of aryl halides in water and surfactants
    Arcadi, A
    Cerichelli, G
    Chiarini, M
    Correa, M
    Zorzan, D
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (20) : 4080 - 4086
  • [48] Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Oxygen-Substituted Allylboronates with Aryl/Vinyl (Pseudo)Halides
    Li, Jie
    Zhang, Xinhui
    Yao, Yisen
    Gao, Yapei
    Yang, Wen
    Zhao, Wanxiang
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (10): : 6951 - 6959
  • [49] Mechanism of palladium-catalyzed decarboxylative cross-coupling between cyanoacetate salts and aryl halides
    JIANG YuanYeFU Yao LIU Lei Department of ChemistryUniversity of Science and Technology of ChinaHefei China Department of ChemistryTsinghua UniversityBeijing China
    中国科学:化学, 2012, 42 (10) : 1493 - 1493
  • [50] Mechanism of palladium-catalyzed decarboxylative cross-coupling between cyanoacetate salts and aryl halides
    JIANG YuanYe
    Science China(Chemistry), 2012, (10) : 2057 - 2062
12345