金鸡纳碱衍生物修饰的负载铱催化剂催化芳香酮不对称加氢

doi:10.3866/PKU.WHXB201304243

Abstract

Abstract:

The asymmetric hydrogenation of aromatic ketones catalyzed by cinchona- and triphenylphosphine (tpp)-modified Ir/SiO₂ was studied. The heterogeneous enantioselective hydrogenation of heterocyclic ketones using a supported iridium catalyst was also investigated. Different analytical techniques, including inductively coupled plasma-atomic emission spectroscopy (ICP-AES), high resolution transmission electron microscopy (HRTEM), X-ray photoelectron spectroscopy (XPS), the Brunauer- Emmett-Teller (BET) method, infrared (IR) spectroscopy, ³¹P solid state nuclear magnetic resonance (NMR) spectroscopy, homogeneous- heterogeneous comparison experiment, conventional filtering test, and mercury poisoning experiment, were used to characterize the catalytic system. HRTEM, XPS, and the BET method clearly characterized the catalytic system. IR and ³¹P solid state NMR spectra provided useful information about the interactions between modifier, metal, and stabilizer. The homogeneous-heterogeneous comparison experiment, conventional filtering test, and mercury poisoning experiment clearly showed the differences between supported, and homogeneous catalysts. In addition, the effects of different stabilizers, modifiers, iridium content, solvents, and base additives on the asymmetric hydrogenation of aromatic ketones were investigated in detail. The results showed that cinchona alkaloids positively modified the Ir/ SiO₂ catalyst. Under the optimum conditions, the hydrogenation enantioselectivities of acetophenone and its derivatives were 52%-96%. The enantioselectivities of the hydrogenation products of 4-acetopyridine, 2-acetothiophene, and 2-acetofuran reached 74%, 75%, and 63%, respectively.

Key words: Iridium, Cinchona alkaloid, Aromatic ketone, Asymmetric hydrogenation, Supported catalyst

JIANG He-Yan, WU Zhi-Feng, CHEN Hua. Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by Cinchona-Modified Ir/SiO₂[J]. Acta Phys. -Chim. Sin. 2013, 29(07), 1572-1581. doi: 10.3866/PKU.WHXB201304243

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Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by Cinchona-Modified Ir/SiO₂

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Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by Cinchona-Modified Ir/SiO2

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Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by Cinchona-Modified Ir/SiO₂