Abstract
Achiral monophosphine TPPTS [TPPTS: P( m-C 6H 4SO 3Na) 3]-stabilized Ru was synthesized by reduction of RuCl 3·3H 2O with hydrogen in ethanol using TPPTS as the stabilizer. The catalytic asymmetric hydrogenation of aromatic ketones using TPPTS-stabilized Ru modified by a chiral diamine (1 R,2 R)-DPENDS [disodium salt of sulfonated (1 R,2 R)-1,2-diphenyl-1,2-ethylene-diamine] was investigated in hydrophilic ionic liquid [RMIM]Ts (1-alkyl-3-methylimidazolium p-methylphenylsulfonates, R = ethyl, butyl, octyl, dodecyl, hexadecyl). Hundred percent conversion and 85.1% ee were obtained for acetophenone under optimized conditions. The resulting products can be easily separated from the catalyst immobilized in ionic liquid by simple extraction with n-hexane, and the catalyst can be reused several times without a significant loss of ee value or conversion. In particular, the addition of water can improve the catalyst performance.
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