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Preparation and use of polymer‐supported chiral ruthenium complex catalyst
Author(s) -
Gao JingXing,
Yi Xiao Dong,
Tang ChunLiang,
Xu PianPian,
Wan HuiLin
Publication year - 2001
Publication title -
polymers for advanced technologies
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.61
H-Index - 90
eISSN - 1099-1581
pISSN - 1042-7147
DOI - 10.1002/pat.93
Subject(s) - ruthenium , acetophenone , catalysis , yield (engineering) , ligand (biochemistry) , benzaldehyde , transfer hydrogenation , polymer chemistry , chemistry , nuclear chemistry , organic chemistry , medicinal chemistry , materials science , biochemistry , receptor , metallurgy
The chiral diiminodiphosphine ligand, [( R,R )‐P 2 N 2 ],has been prepared by the condensation of o ‐(diphenylphosphino)benzaldehyde and 1,2‐diaminocyclohexane. [( R,R )‐P 2 N 2 ] was reduced with excess NaBH 4 in refluxing ethanol to afford the corresponding diaminodiphosphine ligand [( R,R )‐P 2 (NH) 2 ]. The interaction of [( R,R )‐P 2 (NH) 2 ] with trans ‐RuCl 2 (DMSO) 4 gave the chiral ruthenium complex [( R,R )‐RuP 2 (NH) 2 ] in 84% yield. The reaction of [( R,R )‐RuP 2 (NH) 2 ] with poly‐(acrylic acid) using dicyclohexylcarbodiimine as the coupling agent, gave water soluble poly(acrylic acid salt)‐supported chiral ruthenium complex [PAA‐( R,R )‐RuP 2 (NH) 2 ]. These chiral ligands and ruthenium complexes have been fully characterized by microanalysis and IR, NMR spectroscopic methods. The polymer‐bound ruthenium complex [PAA‐( R,R )‐RuP 2 (NH) 2 ] as catalyst was used in asymmetric transfer hydrogenation of acetophenone in 2‐propanol, producing the 1‐phenylethanol in 95% yield and 96% ee. The catalyst was reused twice with some loss of activity and enantioselectivity. Copyright © 2001 John Wiley & Sons, Ltd.