Catalyzed Transfer Hydrogenation of Acetophenone to Phenethyl Alcohol in Water
Abstract: Transfer hydrogenation of acetophenone catalyzed by water-soluble ruthenium complex, RuCl2 (TPPTS)2 [TPPTS: P(m-C6H4SO3Na)3], in the presence of surfactants, was studied. The results showed that the reaction was obviously accelerated by double long-chain cationic surfactants. This was attributed to the formation of vesicles. In this vesicle system, the separation of catalyst and product is simplified after reaction, and the catalyst could be reused for at least 10 times in high conversion.
文章引用: 龙嘉豪 , 方 权 , 刘益美 , 张雨婷 , 马红霞 (2015) 水相体系中苯乙酮催化氢转移制备苯乙醇。 合成化学研究， 3， 1-6. doi: 10.12677/SSC.2015.31001
 Mizushima, E., Ohi, H., Yamaguchi, M., et al. (1999) Asymmetric transfer hydrogenation of aryl-alkyl ketones catalyzed by Ruthenium(II) complexes having chiral pyridylmethylamine and phosphine ligands. Journal of Molecular Catalysis A: Chemical, 149, 43-49.
 Gao, J.X., Yi, X.D., Xu, P.P., et al. (1999) New chiral cationic rhodium-aminophosphine complexes for asymmetric transfer hydrogenation of aromatic ketones. The Journal of Organic Chemistry, 592, 290-295.
 Hashiguchi, S., Fujiii, A., Takehara, J., et al. (1995) Asymmetric transfer hydrogenation of aromatic ketones catalyzed by Chiral Ruthenium(II) Complexes. Journal of the American Chemical Society, 117, 7562-7563.
 Noyori, R. and Hashiguchi, S. (1997) Asymmetric transfer hydrogenation catalyzed by chiral Ruthenium complexes. Accounts of Chemical Research, 30, 97-102.
 Wu, X., Li, X., Hems, W., et al. (2004) Ac-celerated asymmetric transfer hydrogenation of aromatic ketones in water. Organic & Biomolecular Chemistry, 2, 1818-1821.
 Wu, X., Wang, C. and Xiao, J. (2010) Asymmetric transfer hydrogenation in water with platinum group metal catalysts. Platinum Metals Review, 54, 3-19.
 Sun, Y., Liu, G., Gu, H., et al. (2011) Magnetically re-coverable SiO2-coated Fe3O4 nanoparticles: A new platform for asymmetric transfer hydrogenation of aromatic ketones in aqueous medium. Chemical Communications, 47, 2583- 2585.
 Huo, H., Zhou, Z., Zhang, A., et al. (2012) Ru-thenium(II)-catalyzed transfer hydrogenation of aldehydes with new water-soluble monotosylated ethylenediamines as ligands. Research on Chemical Intermediates, 38, 261-268.
 Chaudhari, R.V., Bhanage, B.M., Deshpande, R.M., et al. (1995) Enhancement of interfacial catalysis in a biphasic system using catalyst-binding ligands. Nature, 373, 501-503.
 Cornils, B. and Herrmann, W.A. (2006) Aqueous-phase organometallic catalysis. Wiley-VCH, Wein-heim.
 Dwars, T., Paetzold, E. and Oehme, G. (2005) Reactions in micellar systems. Angewandte Chemie Interna-tional Edition, 44, 7174-7199.
 Li, J., Zhang, Y.M., Han, D.F., Jia, G.Q., Gao, J.B., Zhong, L., et al. (2008) Transfer hydrogenation of aldehydes on amphiphilic catalyst assembled at the interface of emulsion droplets. Green Chemistry, 10, 608-611.
 Schwarze, M., Milano-Brusco, J.S., Strempel, V., Hamerla, T., Wille, S., Fischer, C., et al. (2011) Rhodium catalyzed hydrogenation reactions in aqueous micellar systems as green solvents. RSC Advances, 1, 474-483.
 Kunishima, M., Kikuchi, K., Kawai, Y. and Hioki, K. (2012) Substrate-Selective dehydrocondensation at the interface of micelles and emulsions of common surfactants. Angewandte Chemie International Edition, 51, 2080-2083.
 Li, J.H., Li, X.F., Ma, Y.P., Wu, J.S., Wang, F., Xiang, J., et al. (2013) Surfactant-Accelerated asymmetric transfer hydrogenation with recyclable water-soluble catalyst in aqueous media. RSC Advances, 3, 1825-1834.
 Stephenson, T.A. and Wilkinson, G.J. (1966) New complexes of Ruthenium (II) and (III) with tri-phenylphorostannate, pyridine and other ligands. Journal of Inorganic and Nuclear Chemistry, 28, 945-956.
 Fendler, J.H. (1980) Microemulsions, micelles, and vesicles as media for membrane mimetic photo-chemistry. The Journal of Physical Chemistry, 84, 1485-1491.
 Goedheijt, M.S., Hanson, B.E., Reek, J.N.H., Ka-mer, P.C.J. and van Leeuwen, P.W.N.M. (2000) Accelerated biphasic hydroformylation by vesicle formation of am-phiphilic diphosphines. Journal of the American Chemical Society, 122, 1650-1657.