A new, efficient, and inexpensive copper(II)/salicylic acid complex catalyzed Sonogashira-type cross-coupling of haloarenes and iodoheteroarenes with terminal alkynes

被引:53
|
作者
Chen, Horung-Jyh [1 ]
Lin, Zhe-Yi [1 ]
Li, Meng-Yuan [1 ]
Lian, Ruei-Jheng [1 ]
Xue, Qing-Wen [1 ]
Chung, Jui-Lun [1 ]
Chen, Shu-Chih [1 ]
Chen, Yao-Jung [1 ]
机构
[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan
关键词
Salicylic acid; Sonogashira-type cross-coupling reaction; Copper chloride; Haloarenes; Terminal alkynes; IRON/COPPER COCATALYZED ALKYNYLATION; RAY CRYSTAL-STRUCTURES; EARTH METAL-IONS; COPPER-FREE; ARYL BROMIDES; LIGAND-FREE; AMINE-FREE; PALLADIUM-FREE; CHEMISTRY; HALIDES;
D O I
10.1016/j.tet.2010.07.072
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new, efficient, and inexpensive CuCl2/salicylic acid catalytic system has been developed to catalyze Sonogashira-type cross-coupling of haloarenes and iodoheteroarenes with terminal alkynes under mild reaction conditions to afford the corresponding coupling products in 18-95% yields. The role of salicylic acid might act as a bidentate O,O-donor ligand to activate the catalytic reactivity of copper chloride in coupling reactions was also briefly discussed. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7755 / 7761
页数:7
相关论文
共 50 条
  • [1] 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
    [J]. TETRAHEDRON LETTERS, 2009, 50 (24) : 2865 - 2869
  • [2] A Convenient, Efficient, and Inexpensive Copper(I) Complex Catalyzed Sonogashira Cross-Coupling of o-Iodoanilines with Terminal Alkynes
    Chen, Xia
    Zhou, Xiao-Yu
    [J]. SYNTHESIS-STUTTGART, 2023, 55 (08): : 1213 - 1220
  • [3] Palladium-catalyzed denitrative Sonogashira-type cross-coupling of nitrobenzenes with terminal alkynes
    Feng, Boya
    Yang, Yudong
    You, Jingsong
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (05) : 790 - 793
  • [4] The first palladium-catalyzed desulfitative Sonogashira-type cross-coupling of (hetero)aryl thioethers with terminal alkynes
    Mehta, Vaibhav Pravinchandra
    Sharma, Anuj
    Van der Eycken, Erik
    [J]. ORGANIC LETTERS, 2008, 10 (06) : 1147 - 1150
  • [5] Cu(I)-Catalyzed Macrocyclic Sonogashira-Type Cross-Coupling
    Santandrea, Jeffrey
    Bedard, Anne-Catherine
    Collins, Shawn K.
    [J]. ORGANIC LETTERS, 2014, 16 (15) : 3892 - 3895
  • [6] Ligand-free copper(I)-catalyzed Sonogashira-type coupling of arylboronic acids with terminal alkynes
    Pan, Changduo
    Luo, Fang
    Wang, Wenhui
    Ye, Zhishi
    Cheng, Jiang
    [J]. TETRAHEDRON LETTERS, 2009, 50 (35) : 5044 - 5046
  • [7] Functionalized α,β-ynones: efficient ligand for Cu catalyzed Sonogashira-type cross-coupling reaction
    Wang, Xian
    Wang, Zhenhua
    Xie, Zunyuan
    Zhang, Guofang
    Zhang, Weiqiang
    Gao, Ziwei
    [J]. RSC ADVANCES, 2016, 6 (111) : 109296 - 109300
  • [8] Transition-Metal-Free Sonogashira-Type Cross-Coupling of Alkynes with Fluoroarenes
    Jin, Guanyi
    Zhang, Xuxue
    Cao, Song
    [J]. ORGANIC LETTERS, 2013, 15 (12) : 3114 - 3117
  • [9] Copper- and base-free Sonogashira-type cross-coupling reaction of triarylantimony dicarboxylates with terminal alkynes under an aerobic condition
    Wang, Xuan
    Qin, Weiwei
    Kakusawa, Naoki
    Yasuike, Shuji
    Kurita, Jyoji
    [J]. TETRAHEDRON LETTERS, 2009, 50 (46) : 6293 - 6297
  • [10] Copper-catalyzed enantioselective Sonogashira-type oxidative cross-coupling of unactivated C(sp3)-H bonds with alkynes
    Zhang, Zhen-Hua
    Dong, Xiao-Yang
    Du, Xuan-Yi
    Gu, Qiang-Shuai
    Li, Zhong-Liang
    Liu, Xin-Yuan
    [J]. NATURE COMMUNICATIONS, 2019, 10 (1)