Simple, efficient and recyclable catalytic system for performing copper-catalyzed C-S coupling of thiols with aryl iodides in PEG and PEG-H2O

被引:88
|
作者
She, Jin [1 ]
Jiang, Zheng [1 ]
Wang, Yanguang [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
基金
中国国家自然科学基金;
关键词
ADHESION MOLECULE-1 INTERACTION; ADDITIVE-FREE CONDITIONS; LIGAND-FREE; HIGHLY EFFICIENT; TRANSITION-METAL; DIARYL SULFIDES; BORONIC ACIDS; HALIDES; ARYLATION; VERSATILE;
D O I
10.1016/j.tetlet.2008.11.082
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new protocol for the coupling of aryl iodides with thiophenols or alkanethiols is reported. The reaction is catalyzed by CUI-PEG or Cul-PEG-H2O system in the absence of ligands and volatile organic solvents. A variety of functionalized aryl sulfides are prepared in excellent yields. The isolation of the products is readily performed by the extraction with diethyl ether or petroleum ether, and the Cul-PEG catalyst can be reused without significant loss in activity. The simple catalytic system is economically competitive and environmentally friendly. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:593 / 596
页数:4
相关论文
共 50 条
  • [1] Efficient copper-catalyzed C-S cross-coupling of heterocyclic thiols with aryl iodides
    Niu, Liang-Feng
    Cai, Yan
    Liang, Chao
    Hui, Xin-Ping
    Xu, Peng-Fei
    [J]. TETRAHEDRON, 2011, 67 (16) : 2878 - 2881
  • [2] Ligand-free copper-catalyzed C-S coupling of aryl iodides and thiols
    Sperotto, Elena
    van Klink, Gerard P. M.
    de Vries, Johannes G.
    van Koten, Gerard
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5625 - 5628
  • [3] An Efficient Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides
    Kao, Hsin-Lun
    Chen, Chin-Keng
    Wang, Yu-Jen
    Lee, Chin-Fa
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (09) : 1776 - 1781
  • [4] Efficient ligand-free copper-catalyzed C-S cross-coupling of thiols with aryl iodides using KF/Al2O3 as base
    Feng, Yi-Si
    Li, Yuan-Yuan
    Tang, Lin
    Wu, Wei
    Xu, Hua-Jian
    [J]. TETRAHEDRON LETTERS, 2010, 51 (18) : 2489 - 2492
  • [5] 8-Hydroxyquinolin-N-oxide-Promoted Copper-Catalyzed C-S Cross-Coupling of Thiols with Aryl Iodides
    Su, Kun
    Qiu, Yatao
    Yao, Yiwu
    Zhang, Dayong
    Jiang, Sheng
    [J]. SYNLETT, 2012, (19) : 2853 - 2857
  • [6] Diazaphospholane as an Efficient Ligand for Copper-Catalyzed Cross-Coupling of Thiols with Aryl Iodides
    Yang, Minghua
    Pei, Ji
    Yan, Guobing
    Zheng, Yunfa
    [J]. LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (08) : 587 - 591
  • [7] Efficient C-S Cross-Coupling of Thiols with Aryl Iodides Catalyzed by Cu(OAc)2• H2O and 2,2'- Biimidazole
    Zong, Chenglong
    Liu, Jianli
    Chen, Shengyan
    Zeng, Runsheng
    Zou, Jianping
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2014, 32 (03) : 212 - 218
  • [8] Oxime palladacycle in PEG as a highly efficient and recyclable catalytic system for phenoxycarbonylation of aryl iodides with phenols
    Gaikwad, Vinayak V.
    Bhanage, Bhalchandra M.
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (04)
  • [9] Efficient copper(I)-catalyzed C-S cross coupling of thiols with aryl halides in water
    Rout, Laxmidhar
    Saha, Prasenjit
    Jammi, Suribabu
    Punniyamurthy, Tharmalingam
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (04) : 640 - 643
  • [10] Efficient ligand-free nickel-catalyzed C-S cross-coupling of thiols with aryl iodides
    Jammi, Suribabu
    Barua, Priyanka
    Rout, Laxmidhar
    Saha, Prasenjit
    Punnlyamurthy, Tharmalingam
    [J]. TETRAHEDRON LETTERS, 2008, 49 (09) : 1484 - 1487