A recyclable nanosize aminoarenethiolato copper(I) catalyst for C–C coupling reactions

The attachment of an aminoarenethiolato copper(I) catalyst to a carbosilane dendritic wedge is described. This new catalyst is comparable in activity for the 1,4-addition of diethylzinc to 2-cyclohexenone as the parent catalyst but more robust. In addition, the new catalytic material can be easily r...

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Bibliographic Details
Published inJournal of organometallic chemistry Vol. 689; no. 23; pp. 3813 - 3819
Main Authors Arink, Anne M., van de Coevering, Rob, Wieczorek, Birgit, Firet, Judith, Jastrzebski, Johann T.B.H., Klein Gebbink, Robertus J.M., van Koten, Gerard
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier B.V 15.11.2004
Elsevier
Subjects
Aminoarenethiolate
Carbosilane dendrimer
Catalysis
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Copper catalyst
Nanofiltration
Physical Sciences
Recycling
Science & Technology
Carbosilane dendrimer
Nanofiltration
Copper catalyst
Catalysis
Recycling
Aminoarenethiolate
CORE
carbosilane dendrimer
MOLECULAR-STRUCTURE
catalysis
recycling
DENDRIMERS
nanofiltration
DENDRITIC CATALYSTS
LIGANDS
ENONES
copper catalyst
aminoarenethiolate
1,4-ADDITION
GRIGNARD-REAGENTS
CONJUGATE ADDITION
ARENETHIOLATE
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Summary:The attachment of an aminoarenethiolato copper(I) catalyst to a carbosilane dendritic wedge is described. This new catalyst is comparable in activity for the 1,4-addition of diethylzinc to 2-cyclohexenone as the parent catalyst but more robust. In addition, the new catalytic material can be easily recovered by dialysis from the reaction products and subsequently reused. An aminoarenethiolato copper(I) catalyst was attached to a carbosilane dendritic wedge, which had been prepared via a novel convergent synthetic method. Compared with the unsupported complex, this novel dendritic copper(I) catalyst is more robust towards hydrolysis and oxidation and has increased solubility in common organic solvents. The catalytic activity of the dendritic copper catalyst was tested in the 1,4-addition of Et 2Zn to 2-cyclohexenone. In both polar (Et 2O) and apolar (hexane) solvents excellent activity was observed. The fact that the catalytic copper site remains attached to the nanosize dendritic aminoarenethiolate ligand allows separation of this catalyst by means of nanofiltration.
ISSN:0022-328X
1872-8561
DOI:10.1016/j.jorganchem.2004.07.023