New phosphane based on a beta-cyclodextrin, exhibiting a solvent-tunable conformation, and its catalytic properties.
A new diphenylphosphane based on a beta-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.
Machut-Binkowski
Cécile
C
UniversitéLille Nord de France, 59000 Lille, France.
Legrand
François-Xavier
FX
Azaroual
Nathalie
N
Tilloy
Sébastien
S
Monflier
Eric
E
D002384:Catalysis; D008968:Molecular Conformation; D010720:Phosphines / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D047392:beta-Cyclodextrins / Q000737:chemistry*
D010720:Phosphines; D012997:Solvents; D047392:beta-Cyclodextrins; C044646:phosphine