Palladium() complexes with planar chiral ferrocenyl phosphane-(benz)imidazol-2-ylidene ligands

We describe here the first examples of planar chiral ferrocenyl phosphane-benzimidazol-2-ylidene ligands and their coordination chemistry with palladium( ii ). All ligand precursors, namely enantiopure ferrocenyl phosphane-(benz)imidazolium salts, and all enantiopure palladium complexes have been fu...

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Bibliographic Details
Published in:New journal of chemistry 2014-01, Vol.38 (1), p.338-347
Main Authors: Loxq, Pauline, Debono, Nathalie, Gülcemal, Süleyman, Daran, Jean-Claude, Manoury, Eric, Poli, Rinaldo, Çetinkaya, Bekir, Labande, Agnès
Format: Article
Language:English
Subjects:
Chemical Sciences
Coordination chemistry
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Summary:We describe here the first examples of planar chiral ferrocenyl phosphane-benzimidazol-2-ylidene ligands and their coordination chemistry with palladium( ii ). All ligand precursors, namely enantiopure ferrocenyl phosphane-(benz)imidazolium salts, and all enantiopure palladium complexes have been fully characterised by 1 H, 31 P and 13 C NMR, mass spectrometry and X-ray diffraction methods for seven examples. The potential of these very bulky bidentate ligands in catalysis was evaluated and compared to their imidazol-2-ylidene analogues. The influence of sterics was shown to be non-negligible as the bulkiest ligand gave the lowest activities in the asymmetric Suzuki-Miyaura reaction. Enantiomeric excesses of up to 46% have been obtained in the palladium-catalysed asymmetric Suzuki-Miyaura reaction using very bulky (benz)imidazole-2-ylidene ligands.
ISSN:1144-0546
1369-9261
DOI:10.1039/c3nj00863k