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New Phosphane Based on a β‐Cyclodextrin, Exhibiting a Solvent‐Tunable Conformation, and its Catalytic Properties
Author(s) -
MachutBinkowski Cécile,
Legrand FrançoisXavier,
Azaroual Nathalie,
Tilloy Sébastien,
Monflier Eric
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000379
Subject(s) - hydroformylation , chemistry , moiety , cyclodextrin , solvent , ligand (biochemistry) , solubility , catalysis , regioselectivity , solvent effects , aqueous solution , organic chemistry , rhodium , polymer chemistry , biochemistry , receptor
A new diphenylphosphane based on a β‐cyclodextrin skeleton that exhibits a dual solubility in water and in organic solvent was synthesised. Interestingly, a solvent‐dependent conformation change was evidenced by NMR spectroscopy studies; the self‐inclusion of a phenyl group of the phosphane moiety into cyclodextrin cavity observed in water disappeared in organic solvents due to a change in conformation. Hydrogenation or hydroformylation reactions performed in water and in organic solvents showed that this ligand was able to stabilise catalytically active rhodium species in solution. In the case of the hydroformylation reaction, it was demonstrated that regioselectivity was influenced by the solvent‐dependent conformation of the ligand.