An Effective Activation of Palladium Phosphine Complexes in Aqueous Phase Reactions of Hetero-Aromatic Boronic Acids with Aryl Halides

被引：9
作者：
Bumagin, N. A. [1 ]
Veselov, I. S. [1 ]
Belov, D. S. [1 ]
机构：
[1] Moscow MV Lomonosov State Univ, Moscow 119991, Russia
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2014年 / 50卷 / 01期
基金：
俄罗斯基础研究基金会;
关键词：
heteroaromatic boronic acids; palladium phosphine complexes; water; activation; Suzuki reaction; CROSS-COUPLING REACTIONS; SUBSTITUTED CINNAMIC-ACIDS; SODIUM TETRAPHENYLBORATE; ACRYLIC-ACID; SUZUKI; WATER; HECK; SONOGASHIRA; INHIBITORS; ARYLATION;
D O I：
10.1007/s10593-014-1443-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have developed a simple and effective method for the activation of palladium phosphine complexes in the Suzuki reaction (TON up to 9800, TOF up to 58800 h(-1)) by selecting an aqueous reaction medium instead of organic solvents. This method was elaborated for a high yield synthesis of heteroaromatic biaryls with furyl and thienyl groups.
引用
收藏
页码：19 / 25
页数：7
相关论文
共 46 条
  • [1] A reassessment of the transition-metal free Suzuki-type coupling methodology
    Arvela, RK
    Leadbeater, NE
    Sangi, MS
    Williams, VA
    Granados, P
    Singer, RD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) : 161 - 168
  • [2] Highly efficient palladium-catalyzed boronic acid coupling reactions in water: Scope and limitations
    Badone, D
    Baroni, M
    Cardamone, R
    Ielmini, A
    Guzzi, U
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7170 - 7173
  • [3] Palladium-Catalyzed Direct Arylation of Heteroaromatic Compounds: Improved Conditions Utilizing Controlled Microwave Heating
    Baghbanzadeh, Mostafa
    Pilger, Christian
    Kappe, C. Oliver
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19) : 8138 - 8142
  • [4] Recent progress and current applications of Sonogashira coupling reaction in water
    Bakherad, Mohammad
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (03) : 125 - 140
  • [5] Isoxazol-3-yl(Isothiazol-3-yl)-1,2,4-Triazoles, -Tetrazoles, and-1,3,4-Oxadiazoles: Synthesis, Palladium Complexes, and Catalytic Applications
    Bumagin, N. A.
    Petkevich, S. K.
    Kletskov, A. V.
    Livantsov, M. V.
    Golantsov, N. E.
    Potkin, V. I.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 49 (10) : 1515 - 1529
  • [6] SYNTHESIS OF SUBSTITUTED CINNAMIC-ACIDS BY THE HECK REACTION IN AQUEOUS-MEDIA
    BUMAGIN, NA
    ANDRYUKHOVA, NP
    BELETSKAYA, IP
    [J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1988, 37 (06): : 1285 - 1285
  • [7] PALLADIUM-CATALYZED PHENYLATION AND VINYLATION OF ARYL HALIDES IN AQUEOUS-MEDIA
    BUMAGIN, NA
    BYKOV, VV
    BELETSKAYA, IP
    [J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1990, 39 (11): : 2426 - 2426
  • [8] SYNTHESIS OF DIARYLS FROM PHENYLBORIC ACID AND ARYL IODIDES IN AN AQUEOUS-MEDIUM
    BUMAGIN, NA
    BYKOV, VV
    BELETSKAYA, IP
    [J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1989, 38 (10): : 2206 - 2206
  • [9] SYNTHESIS OF SUBSTITUTED CINNAMIC-ACIDS AND CINNAMONITRILES VIA PALLADIUM CATALYZED COUPLING REACTIONS OF ARYL HALIDES WITH ACRYLIC-ACID AND ACRYLONITRILE IN AQUEOUS-MEDIA
    BUMAGIN, NA
    MORE, PG
    BELETSKAYA, IP
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 371 (03) : 397 - 401
  • [10] BUMAGIN NA, 1990, DOKL AKAD NAUK SSSR+, V315, P1133
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