Palladium-catalysed Heck alkynylation of aryl bromides in an imidazolium ionic liquid: An unexpected subsequent alkyne hydrogenation reaction

被引：18

作者：

Hierso, Jean-Cyrille ^{[1
]}

Picquet, Michel ^{[1
]}

Cattey, Helene ^{[1
]}

Meunier, Philippe ^{[1
]}

机构：

[1] Univ Bourgogne, CNRS, UMR 5188, Lab Synth & Electrosynthese Organomet, F-21078 Dijon, France

来源：

SYNLETT | 2006年 / 18期

关键词：

catalysis; palladium; alkynes; arylation; cross-coupling;

D O I：

10.1055/s-2006-951503

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The copper-free palladium-catalysed alkynylation of aryl bromides with phenylacetylene in the imidazolium ionic liquid [BMIM][BF4], in the presence of triphenylphosphine ligand and pyrrolidine as a base, was found effective and significantly more chemoselective employing deactivated substrates. When activated aryl substrates were used, unexpected side reactions were observed, especially the subsequent hydrogenation of the alkyne function in some coupling products. In other cases, amine arylation reactions occurred, as illustrated by the formation of pyrr olidinyl-4-nitrobenzene, for which an X-ray diffraction structure is reported.

引用

页码：3005 / 3008

页数：4

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