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Enantioselective hydrogenation of α-phenylcinnamic acids over cinchonidine-modified Pd/C commercial catalysts

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Abstract

Enantioselective hydrogenation of α-phenylcinnamic acid (PCA) and p,p′-dimethoxyphenylcinnamic acid (DMPCA) was studied over a variety of commercial 5 % Pd/C catalysts to reveal catalyst properties suitable for obtaining high enantioselectivity. The catalysts were characterized by CO adsorption, X-ray photoelectron spectroscopy (XPS), and transmission electron microscopy (TEM). It is confirmed that pretreatment at 353 K under atmospheric pressure of H2 before modification with cinchonidine is very effective for all the Pd/C catalysts used here to improve the selectivity and reaction rate. It is suggested that the distribution of Pd metal particles is crucial to attain high selectivity (ee% = 79 ± 1 for PCA, 89 ± 2 for DMPCA): a uniform or eggshell-type distribution of Pd is more suitable than an egg-white or egg-yolk-type distribution. It is also suggested that the dispersion of Pd metal particles controls the enantioselectivity over cinchonidine (CD)-modified Pd/C catalysts. XPS techniques are proposed to provide a convenient method to find desirable catalysts. The choice of such Pd/C catalysts could facilitate high-throughput guided study on highly enantioselective hydrogenation of α,β-unsaturated carboxylic acids.

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Acknowledgments

We would like to express our sincere thanks to Evonik Industries AG and N.E. Chemcat Co. for donating the Pd/C catalysts used in the present study.

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Authors and Affiliations

  1. Graduate School of Material Science, University of Hyogo, 3-2-1 Kohto, Kamigori, Ako-Gun, Hyogo, 678-1297, Japan

    Haruka Sato, Takuya Mameda, Kengo Nakai, Tomonori Misaki, Yasuaki Okamoto & Takashi Sugimura

  2. Laboratory of Advanced Science and Technology for Industry, University of Hyogo, 3-2-1 Kohto, Kamigori, Ako-Gun, Hyogo, 678-1297, Japan

    Yuichi Haruyama

  3. Graduate School of Life Science, University of Hyogo, 3-2-1 Kohto, Kamigori, Ako-Gun, Hyogo, 678-1297, Japan

    Seiji Sonobe

  4. Interdisciplinary Graduate School of Science and Engineering, Shimane University, Matsue, 690-8504, Japan

    Takeshi Kubota

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  1. Haruka Sato
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  2. Takuya Mameda
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  3. Kengo Nakai
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  4. Tomonori Misaki
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  7. Takeshi Kubota
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  8. Yasuaki Okamoto
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  9. Takashi Sugimura
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Correspondence to Takashi Sugimura.

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Sato, H., Mameda, T., Nakai, K. et al. Enantioselective hydrogenation of α-phenylcinnamic acids over cinchonidine-modified Pd/C commercial catalysts. Res Chem Intermed 42, 31–45 (2016). https://doi.org/10.1007/s11164-015-2313-x

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