A Simple One-Pot Procedure for the Direct Homocoupling of Terminal Alkynes Promoted by Copper Nanoparticles

被引:47
作者
Nador, Fabiana [1 ]
Fortunato, Leandro [1 ]
Moglie, Yanina [1 ]
Vitale, Cristian [1 ]
Radivoy, Gabriel [1 ]
机构
[1] Univ Nacl Sur, Inst Quim Sur, INQUISUR, CONICET,Dept Quim, RA-8000 Bahia Blanca, Buenos Aires, Argentina
来源
SYNTHESIS-STUTTGART | 2009年 / 23期
关键词
copper nanoparticles; alkynes; dimerizations; coupling; 1,3-diynes; STEREOCONTROLLED TOTAL-SYNTHESIS; CROSS-COUPLING REACTIONS; LIGAND-FREE; HECK REACTIONS; EFFICIENT SYNTHESIS; PALLADIUM CLUSTERS; CARBONYL-COMPOUNDS; ORGANIC-SYNTHESIS; IRON; MACROCYCLES;
D O I
10.1055/s-0029-1217051
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of different terminal alkynes with readily prepared copper(0) nanoparticles led to the formation of the corresponding symmetrical 1,4-disubstituted 1,3-diynes in good yield. No palladium, ligands, or oxidant additives were needed, For aliphatic terminal alkynes, the use of sodium carbonate as base markedly improved the reaction rate and allowed the use of a substoichiometric amount of the copper nanoparticles.
引用
收藏
页码:4027 / 4031
页数:5
相关论文
共 84 条
[1]   A review of modern transition-metal nanoclusters: their synthesis, characterization, and applications in catalysis [J].
Aiken, JD ;
Finke, RG .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 145 (1-2) :1-44
[2]   Hydrodehalogenation of organic halides using the CuCl2.2H2O-Li-arene(cat.) combination [J].
Alonso, F ;
Moglie, Y ;
Radivoy, G ;
Vitale, C ;
Yus, M .
APPLIED CATALYSIS A-GENERAL, 2004, 271 (1-2) :171-176
[3]  
Alonso F, 2003, SYNTHESIS-STUTTGART, P443
[4]   Copper nanoparticles in click chemistry: an alternative catalytic system for the cycloaddition of terminal alkynes and azides [J].
Alonso, Francisco ;
Moglie, Yanina ;
Radivoy, Gabriel ;
Yus, Miguel .
TETRAHEDRON LETTERS, 2009, 50 (20) :2358-2362
[5]   Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis [J].
Astruc, D ;
Lu, F ;
Aranzaes, JR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7852-7872
[6]   Synthesis of poly(aryleneethynylene)s bearing glucose units as substituents [J].
Babudri, F ;
Colangiuli, D ;
Di Lorenzo, PA ;
Farinola, GM ;
Hassan Omar, O ;
Naso, F .
CHEMICAL COMMUNICATIONS, 2003, (01) :130-131
[7]   Requirement for an oxidant in Pd/Cu co-catalyzed terminal alkyne homocoupling give symmetrical 1,4-disubstituted 1,3-diynes [J].
Batsanov, AS ;
Collings, JC ;
Fairlamb, IJS ;
Holland, JP ;
Howard, JAK ;
Lin, ZY ;
Marder, TB ;
Parsons, AC ;
Ward, RM ;
Zhu, J .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :703-706
[8]   First palladium-catalyzed Heck reactions with efficient colloidal catalyst systems [J].
Beller, M ;
Fischer, H ;
Kuhlein, K ;
Reisinger, CP ;
Herrmann, WA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 520 (1-2) :257-259
[9]  
BERSCHEID R, 1992, SYNTHESIS-STUTTGART, P58
[10]   A PROCEDURE FOR THE OXIDATIVE DIMERIZATION OF ALIPHATIC 1-ALKYNES [J].
BRANDSMA, L ;
VERKRUIJSSE, HD ;
WALDA, B .
SYNTHETIC COMMUNICATIONS, 1991, 21 (01) :137-139