Electrochemically Tunable Proton-Coupled Electron Transfer in Pd-Catalyzed Benzaldehyde Hydrogenation

Katherine Koh; Udishnu Sanyal; Mal Soon Lee; Guanhua Cheng; Miao Song; Vassiliki Alexandra Glezakou; Yue Liu; Dongsheng Li; Roger Rousseau; Oliver Y. Gutiérrez; Abhijeet Karkamkar; Miroslaw Derewinski; Johannes A. Lercher

doi:10.1002/anie.201912241

Electrochemically Tunable Proton-Coupled Electron Transfer in Pd-Catalyzed Benzaldehyde Hydrogenation

Katherine Koh, Udishnu Sanyal, Mal Soon Lee, Guanhua Cheng, Miao Song, Vassiliki Alexandra Glezakou, Yue Liu, Dongsheng Li, Roger Rousseau, Oliver Y. Gutiérrez, Abhijeet Karkamkar, Miroslaw Derewinski, Johannes A. Lercher

Research output: Contribution to journal › Article › peer-review

65 Scopus citations

Abstract

Acid functionalization of a carbon support allows to enhance the electrocatalytic activity of Pd to hydrogenate benzaldehyde to benzyl alcohol proportional to the concentration of Brønsted-acid sites. In contrast, the hydrogenation rate is not affected when H₂ is used as a reduction equivalent. The different responses to the catalyst properties are shown to be caused by differences in the hydrogenation mechanism between the electrochemical and the H₂-induced hydrogenation pathways. The enhancement of electrocatalytic reduction is realized by the participation of support-generated hydronium ions in the proximity of the metal particles.

Original language	English
Pages (from-to)	1501-1505
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	4
DOIs	https://doi.org/10.1002/anie.201912241
State	Published - Jan 20 2020
Externally published	Yes

Funding

The research described in this paper is part of the Chemical Transformation Initiative at Pacific Northwest National Laboratory (PNNL), conducted under the Laboratory Directed Research and Development Program at PNNL, a multi-program national laboratory operated by Battelle for the U.S. Department of Energy. Computational resources were provided by PNNL Research Computing. O.Y.G. and M.D. were supported by the U.S. Department of Energy (DOE), Office of Science, Office of Basic Energy Sciences (BES), Division of Chemical Sciences, Geosciences and Biosciences (Transdisciplinary Approaches to Realize Novel Catalytic Pathways to Energy Carriers, FWP 47319). J.A.L. was funded by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) under Germany's Excellence Strategy—EXC 2089/1-390776260.

Funders	Funder number
U.S. Department of Energy
Office of Science
Basic Energy Sciences
Pacific Northwest National Laboratory
Chemical Sciences, Geosciences, and Biosciences Division	FWP 47319
Chemical Sciences, Geosciences, and Biosciences Division
Deutsche Forschungsgemeinschaft	EXC 2089/1-390776260
Deutsche Forschungsgemeinschaft

Keywords

acidity of support
biomass conversion
carbon modification
electrocatalytic hydrogenation
nanocatalysis

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10.1002/anie.201912241

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Koh, K., Sanyal, U., Lee, M. S., Cheng, G., Song, M., Glezakou, V. A., Liu, Y., Li, D., Rousseau, R., Gutiérrez, O. Y., Karkamkar, A., Derewinski, M., & Lercher, J. A. (2020). Electrochemically Tunable Proton-Coupled Electron Transfer in Pd-Catalyzed Benzaldehyde Hydrogenation. Angewandte Chemie - International Edition, 59(4), 1501-1505. https://doi.org/10.1002/anie.201912241

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abstract = "Acid functionalization of a carbon support allows to enhance the electrocatalytic activity of Pd to hydrogenate benzaldehyde to benzyl alcohol proportional to the concentration of Br{\o}nsted-acid sites. In contrast, the hydrogenation rate is not affected when H2 is used as a reduction equivalent. The different responses to the catalyst properties are shown to be caused by differences in the hydrogenation mechanism between the electrochemical and the H2-induced hydrogenation pathways. The enhancement of electrocatalytic reduction is realized by the participation of support-generated hydronium ions in the proximity of the metal particles.",

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Koh, K, Sanyal, U, Lee, MS, Cheng, G, Song, M, Glezakou, VA, Liu, Y, Li, D, Rousseau, R, Gutiérrez, OY, Karkamkar, A, Derewinski, M & Lercher, JA 2020, 'Electrochemically Tunable Proton-Coupled Electron Transfer in Pd-Catalyzed Benzaldehyde Hydrogenation', Angewandte Chemie - International Edition, vol. 59, no. 4, pp. 1501-1505. https://doi.org/10.1002/anie.201912241

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T1 - Electrochemically Tunable Proton-Coupled Electron Transfer in Pd-Catalyzed Benzaldehyde Hydrogenation

AU - Koh, Katherine

AU - Sanyal, Udishnu

AU - Lee, Mal Soon

AU - Cheng, Guanhua

AU - Song, Miao

AU - Glezakou, Vassiliki Alexandra

AU - Liu, Yue

AU - Li, Dongsheng

AU - Rousseau, Roger

AU - Gutiérrez, Oliver Y.

AU - Karkamkar, Abhijeet

AU - Derewinski, Miroslaw

AU - Lercher, Johannes A.

PY - 2020/1/20

Y1 - 2020/1/20

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AB - Acid functionalization of a carbon support allows to enhance the electrocatalytic activity of Pd to hydrogenate benzaldehyde to benzyl alcohol proportional to the concentration of Brønsted-acid sites. In contrast, the hydrogenation rate is not affected when H2 is used as a reduction equivalent. The different responses to the catalyst properties are shown to be caused by differences in the hydrogenation mechanism between the electrochemical and the H2-induced hydrogenation pathways. The enhancement of electrocatalytic reduction is realized by the participation of support-generated hydronium ions in the proximity of the metal particles.

KW - acidity of support

KW - biomass conversion

KW - carbon modification

KW - electrocatalytic hydrogenation

KW - nanocatalysis

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JF - Angewandte Chemie - International Edition

IS - 4

ER -

Electrochemically Tunable Proton-Coupled Electron Transfer in Pd-Catalyzed Benzaldehyde Hydrogenation

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