Controlled mono and double Heck reactions in water catalyzed by an oxime-derived palladacycle

被引:94
作者
Botella, L
Nájera, C
机构
[1] Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain
[2] Univ Alicante, ISO, E-03080 Alicante, Spain
关键词
alkenes; diarylations; Heck reaction; palladacycle; palladium catalysis;
D O I
10.1016/j.tetlet.2004.01.024
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The mono and beta,beta-diarylation of alpha,beta-unsaturated carbonyl compounds with electron-deficient and electron-rich aromatic iodides in water is described. These reactions are catalyzed by the p-hydroxyacetophenone oxime-derived palladacycle 1 by controlling the stoichiometry of the aryl iodide and the alkene as well as the loading of the palladium catalyst. This one-pot protocol is performed in refluxing water and (dicyclohexyl)methylamine as base under thermal or microwave conditions and in the absence of an inert atmosphere. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1833 / 1836
页数:4
相关论文
共 45 条
[1]   Oxime palladacycles:: Stable and efficient catalysts for carbon-carbon coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
ORGANIC LETTERS, 2000, 2 (13) :1823-1826
[2]   Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5588-5594
[3]   C(sp2)-C(sp) and C(sp)-C(sp) coupling reactions catalyzed by oxime-derived palladacycles [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) :1146-1158
[4]   A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
TETRAHEDRON LETTERS, 2002, 43 (51) :9365-9368
[5]  
Alonso DA, 2002, ADV SYNTH CATAL, V344, P172, DOI 10.1002/1615-4169(200202)344:2<172::AID-ADSC172>3.0.CO
[6]  
2-9
[7]  
Amengual R, 2002, ADV SYNTH CATAL, V344, P393, DOI 10.1002/1615-4169(200206)344:3/4<393::AID-ADSC393>3.0.CO
[8]  
2-K
[9]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[10]   Cross-coupling reactions with boronic acids in water catalysed by oxime-derived palladacycles [J].
Botella, L ;
Nájera, C .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 663 (1-2) :46-57