Synthesis of symmetrical 1,3-diynes via homocoupling reaction of n-butyl alkynyltellurides

被引:33
作者
Singh, Fateh V. [1 ]
Amaral, Monica F. Z. J. [1 ]
Stefani, Helio A. [1 ,2 ]
机构
[1] Univ Sao Paulo, Fac Ciencias Farmaceut, BR-05508900 Sao Paulo, Brazil
[2] Univ Fed Sao Paulo, Dept Biofis, Sao Paulo, Brazil
基金
巴西圣保罗研究基金会;
关键词
Homocoupling reaction; Symmetrical 1,3-diynes; Alkynyltellurides; CROSS-COUPLING REACTION; ALKYL-HALIDES; EFFICIENT SYNTHESIS; LIQUID-CRYSTALS; TELLURIDES; ULTRASOUND; CATALYSTS; ROUTE;
D O I
10.1016/j.tetlet.2009.03.078
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An ultrasound-assisted synthesis of symmetrical 1,3-diyne compounds with electron-withdrawing or donating substituents is described and illustrated by the palladium-catalyzed homocoupling reaction of n-butyl alkynyltellurides. This procedure offers easy access to 1,3-diynes in very short reaction times, and the products are achieved in good to excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2636 / 2639
页数:4
相关论文
共 69 条
[1]  
[Anonymous], TELLURIUM ORGANIC CH
[2]   A NEW AND EFFICIENT REACTION FOR THE SYNTHESIS OF THE CARBON-CARBON BOND [J].
BARTON, DHR ;
OZBALIK, N ;
RAMESH, M .
TETRAHEDRON LETTERS, 1988, 29 (29) :3533-3536
[3]   Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens [J].
Bedford, RB ;
Bruce, DW ;
Frost, RM ;
Hird, M .
CHEMICAL COMMUNICATIONS, 2005, (33) :4161-4163
[4]  
BLANGETTI M, 2007, EUR J ORG CHEM, P5867
[5]   Sonogashira cross-coupling reaction of organotellurium dichlorides with terminal alkynes [J].
Braga, AL ;
Lüdtke, DS ;
Vargas, F ;
Donato, RK ;
Silveira, CC ;
Stefani, MA ;
Zeni, G .
TETRAHEDRON LETTERS, 2003, 44 (09) :1779-1781
[6]  
BUNZ UHF, 2000, ACCOUNTS CHEM RES, V33, P791
[7]  
Cadiot P., 1969, CHEM ACETYLENES, P597
[8]   Iron-catalyzed homo-coupling of simple and functionalized arylmagnesium reagents [J].
Cahiez, G ;
Chaboche, C ;
Mahuteau-Betzer, F ;
Ahr, M .
ORGANIC LETTERS, 2005, 7 (10) :1943-1946
[9]  
Cahiez G, 1998, SYNTHESIS-STUTTGART, P1199
[10]   Manganese- or iron-catalyzed homocoupling of Grignard reagents using atmospheric oxygen as an oxidant [J].
Cahiez, Gerard ;
Moyeux, Alban ;
Buendia, Julien ;
Duplais, Christophe .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13788-+