An efficient approach to homocoupling of terminal alkynes: Solvent-free synthesis of 1,3-diynes using catalytic Cu(II) and base

被引:121
作者
Wang, Dong
Li, Jihui
Li, Na
Gao, Tingting
Hou, Sihua
Chen, Baohua [1 ]
机构
[1] Key Lab Nonferrous Met Chem & Resources Utilizat, Lanzhou 730000, Peoples R China
基金
美国国家科学基金会;
关键词
COUPLING REACTION; CHEMISTRY; DIYNES;
D O I
10.1039/b917448f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report an environmentally friendly, efficient method for transforming terminal acetylenes into 1,3-diynes based on catalytic amounts of a Cu(II) salt and base under solvent-free conditions. The developed process conforms to the principles of 'green' chemistry and addresses the shortage of such methods for the synthesis of 1,3-diynes. The reaction is quite general and results in good yields. Interestingly, the system also allows the synthesis of unsymmetric 1,3-diynes by cross-coupling of two different terminal alkynes. Finally, the catalyst can also be recycled.
引用
收藏
页码:45 / 48
页数:4
相关论文
共 34 条
[21]   Amine- and phosphine-free palladium(II)-catalyzed homocoupling reaction of terminal alkynes [J].
Li, JH ;
Yun, L ;
Zhang, XD .
TETRAHEDRON, 2005, 61 (07) :1903-1907
[22]   A facile synthesis of diynes [J].
Liu, QB ;
Burton, DJ .
TETRAHEDRON LETTERS, 1997, 38 (25) :4371-4374
[23]  
Matlack A. S., 2001, Introduction to Green Chemistry
[24]   CYTOTOXIC ACTIVITY OF POLYACETYLENE COMPOUNDS IN PANAX-GINSENG MEYER,C.A. [J].
MATSUNAGA, H ;
KATANO, M ;
YAMAMOTO, H ;
FUJITO, H ;
MORI, M ;
TAKATA, K .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (12) :3480-3482
[25]  
OISHI T, 2009, CHEM EUR J
[26]   A principled stance [J].
Poliakoff, M ;
Anastas, P .
NATURE, 2001, 413 (6853) :257-257
[27]   Modified Glaser reaction of terminal alkynes on KF/alumina [J].
Sharifi, A ;
Mirzaei, M ;
Naimi-Jamal, MR .
MONATSHEFTE FUR CHEMIE, 2006, 137 (02) :213-217
[28]   NHC-Pd(II) complex-Cu(I) co-catalyzed homocoupling reaction of terminal alkynes [J].
Shi, Min ;
Qian, Heng-xin .
APPLIED ORGANOMETALLIC CHEMISTRY, 2006, 20 (11) :771-774
[29]  
Siemsen P, 2000, ANGEW CHEM INT EDIT, V39, P2633
[30]   CONVENIENT SYNTHESIS OF ACETYLENES - CATALYTIC SUBSTITUTIONS OF ACETYLENIC HYDROGEN WITH BROMOALKENES, IODOARENES, AND BROMOPYRIDINES [J].
SONOGASHIRA, K ;
TOHDA, Y ;
HAGIHARA, N .
TETRAHEDRON LETTERS, 1975, (50) :4467-4470