Imidazol(in)ium carboxylates as N-heterocyclic carbene ligand precursors for Suzuki-Miyaura reactions

aryl halides; boronic acids; homogeneous catalysis; N-heterocyclic carbene ligands; palladium and compounds; stilbenes; Suzuki-Miyaura coupling reactions

Abstract :

[en] Simple catalysts formed in situ from palladium acetate and a variety of imidazolium and imidazolinium carboxylates and dithiocarboxylates have been screened in the coupling of aryl halides with trans-2-phenylvinylboronic acid. Imidazol(in)ium carboxylates show an excellent activity, which compares to that displayed by the parent imidazol(in)ium chlorides, whereas imidazol(in)ium dithiocarboxylates are poorly efficient. Interestingly, the base employed exerts a profound influence on the trans/cis stereochemistry of the coupling product. (c) 2006 Elsevier Ltd. All rights reserved.

Disciplines :

Chemistry

Author, co-author :

Tudose, Adriana

Delaude, Lionel ; Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique

André, Benoît

Demonceau, Albert ; Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique

Language :

English

Title :

Imidazol(in)ium carboxylates as N-heterocyclic carbene ligand precursors for Suzuki-Miyaura reactions

Publication date :

2006

Journal title :

Tetrahedron Letters

ISSN :

0040-4039

Publisher :

Pergamon-Elsevier Science Ltd, Oxford, United Kingdom

Volume :

Issue :

Pages :

8529-8533

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 26 June 2009

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Reaction conditions: Pd(OAc)2, 0.01 mmol; imidazolium chloride 8a, 0.04 mmol; Na2CO3, 4 mmol; trans-4-methoxystilbene, 2.0 mmol; 1,4-dioxane, 3 mL; 80 °C, under an inert atmosphere of nitrogen for 150 h.
Pd(OAc)2, 0.01 mmol; imidazolium chloride 8a, 0.04 mmol; Li2CO3 or Na2CO3, 2 mmol; trans-4-methoxystilbene, 1.0 mmol; trans-2-phenylvinylboronic acid, 0.2 mmol; 1,4-dioxane, 3 mL; 80 °C, under an inert atmosphere of nitrogen for 150 h.