Acta Phys. -Chim. Sin. ›› 2007, Vol. 23 ›› Issue (09): 1381-1386.doi: 10.3866/PKU.WHXB20070914

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Asymmetric Hydrogenation of Acetophenone and Its Derivatives Catalyzed by Ruthenium Nanoparticles in Ionic Liquid Media

WANG Jin-Bo; MING Fang-Yong; JIANG Wei-Dong; FAN Guang-Yin; LIU De-Rong; CHEN Hua; LI Xian-Jun   

  1. Key Laboratory of Green Chemistry and Technology of the Ministry of Education, Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
  • Received:2007-03-15 Revised:2007-05-24 Published:2007-09-06
  • Contact: CHEN Hua E-mail:scuhchen@163.com

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Abstract: Reduction of RuCl3·3H2O with hydrogen in ionic liquid [BMIM]BF4(1-butyl-3-methylimidazolium tetrafluoroborate) or [BMIM][p-CH3C6H4SO3] (1-butyl-3-methylimidazolium p-methylphenylsulfonate) medium using P(m-C6H4SO3Na)3 (TPPTS) as stabilizer yielded ruthenium nanoparticles. Further treatment of the Ru nanoparticles with chiral modifier (1S, 2S)-1,2-diphenyl-1,2-ethylene-diamine((1S, 2S)-DPEN) and KOHin ionic liquid/i-PrOH mixed solvent resulted in a novel immobilized chiral catalyst which can asymmetrically hydrogenate acetophenone and its derivatives. 100%conversion and 79.1%ee (enantiomeric excess) were obtained for acetophenone under optimized conditions. The catalyst immobilized in ionic liquid not only exhibits excellent reactivities and enantioselectivities in asymmetric hydrogenation of acetophenone and its derivatives, but also can be recycled and reused by simple extraction with n-hexane.

Key words: Nano-Ru, Ionic liquids, Aromatic ketones, Asymmetric hydrogenation