Copper-catalyzed cross-coupling reactions of bromoalkynols with terminal alkynes in supercritical carbon dioxide

被引:49
作者
Jiang, Huan-Feng [1 ]
Wang, A-Zhong [1 ]
机构
[1] S China Univ Technol, Coll Chem, Guangzhou 510640, Peoples R China
来源
SYNTHESIS-STUTTGART | 2007年 / 11期
关键词
unsymmetrical diynes; heterocoupling reaction; alkynes; supercritical carbon dioxide;
D O I
10.1055/s-2007-966058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-catalyzed cross-coupling reactions of bromoalkynols and terminal alkynes were carried out in supercritical carbon dioxide (SCCO2) to afford the corresponding unsymmetrical diynes with good yields. The reaction is sensitive to temperature and the pressure of CO,. Methanol, as a cosolvent of scCO(2), could promote dissolution of the inorganic salt and thus facilitated the reaction. This new heterocoupling reaction system is more environmentally friendly than more traditional methods, since it uses scCO(2) as solvent and sodium acetate as base instead of amines.
引用
收藏
页码:1649 / 1654
页数:6
相关论文
共 33 条
  • [1] A convenient route to unsymmetrical conjugated diynes
    Alami, M
    Ferri, F
    [J]. TETRAHEDRON LETTERS, 1996, 37 (16) : 2763 - 2766
  • [2] Synthesis of polyacetylenic acids isolated from Nanodea muscosa
    Alves, D
    Nogueira, CW
    Zeni, G
    [J]. TETRAHEDRON LETTERS, 2005, 46 (50) : 8761 - 8764
  • [3] NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE
    AMATORE, C
    BLART, E
    GENET, JP
    JUTAND, A
    LEMAIREAUDOIRE, S
    SAVIGNAC, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6829 - 6839
  • [4] Cadiot P., 1969, Chemistry of Acetylenes, P597
  • [5] Palladium-catalyzed regioselective cyclotrimerization of acetylenes in supercritical carbon dioxide
    Cheng, JS
    Jiang, HF
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (03) : 643 - 646
  • [6] Chodkiewicz W., 1957, ANN CHIM PARIS, V2, P819
  • [7] Reactions in unusual media
    Clarke, D
    Ali, MA
    Clifford, AA
    Parratt, A
    Rose, P
    Schwinn, D
    Bannwarth, W
    Rayner, CM
    [J]. CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2004, 4 (07) : 729 - 771
  • [8] Synthesis of (Z)-1-phenylseleno-1,4-diorganyl-1-buten-3-ynes:: hydroselenation of symmetrical and unsymmetrical 1,4-diorganyl-1,3-butadiynes
    Dabdoub, MJ
    Baroni, ACM
    Lenardâo, EJ
    Gianeti, TR
    Hurtado, GR
    [J]. TETRAHEDRON, 2001, 57 (20) : 4271 - 4276
  • [9] New directions in inorganic and metal-organic coordination chemistry in supercritical fluids
    Darr, JA
    Poliakoff, M
    [J]. CHEMICAL REVIEWS, 1999, 99 (02) : 495 - 541
  • [10] Total synthesis of two naturally occurring polyacetylenic glucosides (-)-bidensyneoside A1 and B, and an analogue of (-)-bidensyneoside C
    Gung, BW
    Fox, RM
    Falconer, R
    Shissler, D
    [J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (01) : 40 - 46