Ethanol-promoted reductive homocoupling reactions of aryl halides catalyzed by palladium on carbon (Pd/C)

被引：36
|
作者：
Shao, Linjun [1 ]
Du, Yijun [2 ]
Zeng, Minfeng [1 ]
Li, Xiudong [1 ]
Shen, Wenting [1 ]
Zuo, Shufeng [1 ]
Lu, Yueqing [1 ]
Zhang, Xian-Man [1 ]
Qi, Chenze [1 ]
机构：
[1] Shaoxing Univ, Inst Appl Chem, Shaoxing 312000, Zhejiang, Peoples R China
[2] Shaoxing Univ, Coll Yuanpei, Shaoxing 312000, Zhejiang, Peoples R China
来源：
APPLIED ORGANOMETALLIC CHEMISTRY | 2010年 / 24卷 / 05期
关键词：
palladium; biaryls; aryl halides; homocoupling; ethanol; INTRAMOLECULAR COUPLING REACTIONS; ULLMANN REACTION; BOND FORMATION; WATER; COMPLEXES; ZINC;
D O I：
10.1002/aoc.1635
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Homocoupling reactions of aryl bromides or iodides proceeded smoothly with palladium on carbon (Pd/C) catalyst, ethanol and base in dimethyl sulfoxide (DMSO) to afford exclusively symmetric biaryls in good to excellent yields. Ethanol was first used as a reducing agent in situ to reduce the Pd2+/C species into Pd-0/C active species to complete the catalytic redox cycle. It was found that ethanol can promote the Pd/C-catalyzed reductive homocoupling of aryl iodides and bromides efficiently in the presence of base. A reaction mechanism has been put forward and discussed. Copyright (C) 2010 John Wiley & Sons, Ltd.
引用
收藏
页码：421 / 425
页数：5
相关论文
共 50 条
  • [1] Tetrakis(dimethylamino)ethylene (TDAE)-Pd promoted reductive homocoupling of aryl halides
    Kuroboshi, M
    Waki, Y
    Tanaka, H
    SYNLETT, 2002, (04) : 637 - 639
  • [2] Indium promoted reductive homocoupling of alkyl and aryl halides
    Ranu, BC
    Dutta, P
    Sarkar, A
    TETRAHEDRON LETTERS, 1998, 39 (51) : 9557 - 9558
  • [3] Palladium/Sensory Component-Catalyzed Homocoupling Reactions of Aryl Halides
    Bao, Fengyu
    Liu, Zhikai
    Bai, Haixin
    Zhang, Haiyan
    Liu, Pengfei
    Zhang, Qidong
    Chai, Guobi
    SYNLETT, 2020, 31 (15) : 1501 - 1506
  • [4] Direct homocoupling of aryl halides catalyzed by palladium
    Penalva, V
    Hassan, J
    Lavenot, L
    Gozzi, C
    Lemaire, M
    TETRAHEDRON LETTERS, 1998, 39 (17) : 2559 - 2560
  • [5] Palladium catalyzed reductive homocoupling reactions of aromatic halides in dimethyl sulfoxide (DMSO) solution
    Qi, Chenze
    Sun, Xudong
    Lu, Cuiyun
    Yang, Jinzhi
    Du, Yijun
    Wu, Huajiang
    Zhang, Xian-Man
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (18) : 2912 - 2916
  • [6] Palladium-Catalyzed Reductive Homocoupling of Aromatic Halides and Oxidation of Alcohols
    Zeng, Minfeng
    Du, Yijun
    Shao, Linjun
    Qi, Chenze
    Zhang, Xian-Man
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (08): : 2556 - 2563
  • [7] Palladium-catalyzed tetrakis(dimethylamino)ethylene-promoted reductive coupling of aryl halides
    Kuroboshi, M
    Waki, Y
    Tanaka, H
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10): : 3938 - 3942
  • [8] 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
  • [9] Palladium/Sensory Component-Catalyzed Homocoupling Reactions of Aryl Halides (vol 31, pg 1501, 2020)
    Bao, Fengyu
    Liu, Zhikai
    Bai, Haixin
    Zhang, Haiyan
    Liu, Pengfei
    Zhang, Qidong
    Chai, Guobi
    SYNLETT, 2020, 31 (17) : 1740 - 1740
  • [10] Palladium-Catalyzed Asymmetric Reductive Heck Reaction of Aryl Halides
    Yue, Guizhou
    Lei, Kaining
    Hirao, Hajime
    Zhou, Jianrong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (22) : 6531 - 6535
12345