The thermoregulated ligand-palladium-catalyzed carbonylative Sonogashira coupling of aryl iodides with terminal alkynes in water

被引:9
|
作者
Hao, Yuanping [1 ]
Jiang, Jingyang [1 ]
Wang, Yanhua [1 ]
Jin, Zilin [1 ]
机构
[1] Dalian Univ Technol, Fac Chem Environm & Biol Sci & Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
关键词
alkynones; palladium; carbonylative; Sonogashira coupling; thermoregulated phase-transfer catalysis; PHASE-TRANSFER LIGANDS; AQUEOUS/ORGANIC BIPHASIC SYSTEM; 2-PHASE HYDROFORMYLATION; ACID-CHLORIDES; EFFICIENT; DERIVATIVES; KETONES; COMPLEX; HYDROGENATION; AZASPIRACIDS;
D O I
10.1002/aoc.3337
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The carbonylative Sonogashira coupling of aryl iodides with terminal alkynes was studied by using thermoregulated ligand-palladium as an efficient and reusable catalyst at 80 degrees C in water. The corresponding alkynone products were obtained in good to excellent yields under 1atm of carbon monoxide. The isolation of the products was readily achieved by extraction with ethyl acetate, and the catalyst recovered in water can be reused and recycled up to four times without significant loss in catalytic activity. Copyright (c) 2015 John Wiley & Sons, Ltd.
引用
收藏
页码:608 / 611
页数:4
相关论文
共 50 条
  • [31] A Novel Protocol for the Cu-Catalyzed Sonogashira Coupling Reaction between Aryl Halides and Terminal Alkynes using trans-1,2-Diaminocyclohexane Ligand
    Asha, Sujatha
    Thomas, Anns Maria
    Ujwaldev, Sankuviruthiyil M.
    Anilkumar, Gopinathan
    CHEMISTRYSELECT, 2016, 1 (13): : 3938 - 3941
  • [32] 2,2′-Diamino-6,6′-dimethylbiphenyl as an Efficient Ligand in the CuI-Catalyzed Sonogashira Reaction of Aryl Iodides and Bromides with Terminal Alkynes
    Wang, Bin-Bin
    Ye, Yue-Mei
    Chen, Jun-Jun
    Zhou, Xia-Xia
    Lu, Jian-Mei
    Shao, Li-Xiong
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2011, 84 (05) : 526 - 530
  • [33] Efficient Copper-Catalyzed Sonogashira Couplings of Aryl Halides with Terminal Alkynes in Water
    Yang, Daoshan
    Li, Bing
    Yang, Haijun
    Fu, Hua
    Hu, Liming
    SYNLETT, 2011, (05) : 702 - 706
  • [34] Palladium-Catalyzed Carbonylative Synthesis of α-Branched Enones from Aryl Iodides and Arylallenes
    Geng, Hui-Qing
    Wang, Le-Cheng
    Hou, Chen-Yang
    Wu, Xiao-Feng
    ORGANIC LETTERS, 2020, 22 (03) : 1160 - 1163
  • [35] An efficient copper(I) complex catalyzed Sonogashira type cross-coupling of aryl halides with terminal alkynes
    Thakur, K. G.
    Jaseer, E. A.
    Naidu, Ajay B.
    Sekar, Govindasamy
    TETRAHEDRON LETTERS, 2009, 50 (24) : 2865 - 2869
  • [36] Palladium-Catalyzed Regioselective Heck Coupling of Alkynes with Aryl Iodides for the Synthesis of Trisubstituted Allenes
    Lv, Weiwei
    Chen, Yanhui
    Zhao, Zemin
    Wen, Si
    Cheng, Guolin
    ORGANIC LETTERS, 2019, 21 (19) : 7795 - 7798
  • [37] A General Palladium-Catalyzed Sonogashira Coupling of Aryl and Heteroaryl Tosylates
    R'kyek, Omar
    Halland, Nis
    Lindenschmidt, Andreas
    Alonso, Jorge
    Lindemann, Peter
    Urmann, Matthias
    Nazare, Marc
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (33) : 9986 - 9989
  • [38] Palladium-catalyzed Sonogashira cross-coupling of organic tellurides with alkynes
    Kawaguchi, Shin-ichi
    Srivastava, Puneet
    Engman, Lars
    TETRAHEDRON LETTERS, 2011, 52 (32) : 4120 - 4122
  • [39] Palladium-Catalyzed Carbonylative Cross-Coupling of Aryl Iodides and Alkenyl Bromides with Benzyl Halides under Reductive Conditions
    Lin, Tingzhi
    Qian, Pengcheng
    Wang, Yan-En
    Ou, Mingjie
    Cui, Ning
    Ye, Yu
    Hua, Rui
    Xiong, Dan
    Xue, Fei
    Walsh, Patrick J.
    Mao, Jianyou
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (12)
  • [40] Palladium-catalyzed carbonylative synthesis of acylstannanes from aryl iodides and hexamethyldistannane
    Chen, Bo
    Yuan, Yang
    Xu, Jian-Xing
    Franke, Robert
    Wu, Xiao-Feng
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2020, 923 (923)