Copper(I) iodide-DMAP catalyzed homo- and heterocoupling of terminal alkynes

被引:49
作者
Navale, Balu S. [1 ]
Bhat, Ramakrishna G. [1 ]
机构
[1] IISER, Dept Chem, Pune 411008, Maharashtra, India
来源
RSC ADVANCES | 2013年 / 3卷 / 15期
关键词
HOMOCOUPLING REACTION; COUPLING REACTIONS; ROOM-TEMPERATURE; PALLADIUM; OXIDANT; ROUTE; BASES;
D O I
10.1039/c3ra23478a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A practical and efficient catalytic system comprising CuI and DMAP has been developed for the oxidative homo-and heterocoupling of terminal alkynes under aerobic conditions at room temperature. The catalytic utility of DMAP for efficient oxidative coupling of terminal alkynes has been explored. The CuI-DMAP catalytic system avoids the need for excess base and specialized ligands in oxidative coupling. Short reaction times make this approach economical and environmentally friendly.
引用
收藏
页码:5220 / 5226
页数:7
相关论文
共 41 条
  • [1] Influence of Bases and Ligands on the Outcome of the Cu(I)-Catalyzed Oxidative Homocoupling of Terminal Alkynes to 1,4-Disubstituted 1,3-Diynes Using Oxygen as an Oxidant
    Adimurthy, Subbarayappa
    Malakar, Chandi C.
    Beifuss, Uwe
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) : 5648 - 5651
  • [2] C(sp2)-C(sp) and C(sp)-C(sp) coupling reactions catalyzed by oxime-derived palladacycles
    Alonso, DA
    Nájera, C
    Pacheco, MC
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) : 1146 - 1158
  • [3] Heterogeneous Catalytic Homocoupling of Terminal Alkynes
    Alonso, Francisco
    Yus, Miguel
    [J]. ACS CATALYSIS, 2012, 2 (07): : 1441 - 1451
  • [4] Homocoupling of Terminal Alkynes Catalysed by Ultrafine Copper Nanoparticles on Titania
    Alonso, Francisco
    Melkonian, Taki
    Moglie, Yanina
    Yus, Miguel
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (13) : 2524 - 2530
  • [5] Efficient Copper(II) Acetate Catalyzed Homo- and Heterocoupling of Terminal Alkynes at Ambient Conditions
    Balaraman, Kaluvu
    Kesavan, Venkitasamy
    [J]. SYNTHESIS-STUTTGART, 2010, (20): : 3461 - 3466
  • [6] Requirement for an oxidant in Pd/Cu co-catalyzed terminal alkyne homocoupling give symmetrical 1,4-disubstituted 1,3-diynes
    Batsanov, AS
    Collings, JC
    Fairlamb, IJS
    Holland, JP
    Howard, JAK
    Lin, ZY
    Marder, TB
    Parsons, AC
    Ward, RM
    Zhu, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) : 703 - 706
  • [7] Synthesis of a small library of bivalent α-D-mannopyranosides for lectin cross-linking
    Bergeron-Brlek, Milan
    Shiao, Tze Chieh
    Trono, M. Corazon
    Roy, Rene
    [J]. CARBOHYDRATE RESEARCH, 2011, 346 (12) : 1479 - 1489
  • [8] Bullock R. M., 2010, Catalysis without Precious Metals
  • [9] An Unusual Nickel-Copper-Mediated Alkyne Homocoupling Reaction for the Active-Template Synthesis of [2]Rotaxanes
    Crowley, James D.
    Goldup, Stephen M.
    Gowans, Nicholas D.
    Leigh, David A.
    Ronaldson, Vicki E.
    Slawin, Alexandra M. Z.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) : 6243 - 6248
  • [10] Diederich F, 2005, ACETYLENE CHEMISTRY: CHEMISTRY, BIOLOGY AND MATERIAL SCIENCE, pV