Microwave-heated γ-Alumina Applied to the Reduction of Aldehydes to Alcohols

Bhausaheb Dhokale; Arturo Susarrey-Arce; Anna Pekkari; August Runemark; Kasper Moth-Poulsen; Christoph Langhammer; Hanna Härelind; Michael Busch; Matthias Vandichel; Henrik Sundén

doi:10.1002/cctc.202001284

Microwave-heated γ-Alumina Applied to the Reduction of Aldehydes to Alcohols

Bhausaheb Dhokale, Arturo Susarrey-Arce, Anna Pekkari, August Runemark, Kasper Moth-Poulsen, Christoph Langhammer, Hanna Härelind, Michael Busch, Matthias Vandichel, Henrik Sundén^*

^*Corresponding author for this work

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

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Abstract

The development of cheap and robust heterogeneous catalysts for the Meerwein-Ponndorf-Verley (MPV) reduction is desirable due to the difficulties in product isolation and catalyst recovery associated with the traditional use of homogeneous catalysts for MPV. Herein, we show that microwave heated γ-Al₂O₃ can be used for the reduction of aldehydes to alcohols. The reaction is efficient and has a broad substrates scope (19 entries). The products can be isolated by simple filtration, and the catalyst can be regenerated. With the use of microwave heating, we can direct the heating to the catalyst rather than to the whole reaction medium. Furthermore, DFT was used to study the reaction mechanism, and we can conclude that a dual-site mechanism is operative where the aldehyde and 2-propoxide are situated on two adjacent Al sites during the reduction. Additionally, volcano plots were used to rationalize the reactivity of Al₂O₃ in comparison to other metal oxides.

Original language	English
Pages (from-to)	6344-6355
Number of pages	12
Journal	ChemCatChem
Volume	12
Issue number	24
Early online date	23 Oct 2020
DOIs	https://doi.org/10.1002/cctc.202001284
Publication status	Published - 16 Dec 2020
MoE publication type	A1 Journal article-refereed

Funding

Formas (2016‐00484) is gratefully acknowledged for funding. H. S., B. D., A. S‐A., C. L., K. M.‐P. and A. P. would also like to thank Knut and Alice Wallenberg Foundation for support via project 2015.0055. Computational resources and services used for this work were provided by C3SE (Göteborg) and ICHEC (Ireland). H. H. also acknowledge the Competence Centre for Catalysis hosted by Chalmers University of Technology and financially supported by the Swedish Energy Agency and the member companies AB Volvo, ECAPS AB, Johnson Matthey AB, Preem AB, Scania CV AB, Umicore Denmark ApS and Volvo Car Corporation AB. A.S.‐A. would like to thank Dr. Dirk Niemeyer from Sasol Limited for the provided γ‐AlO samples. 2 3

Keywords

Microwave-assisted catalysis
MPV reduction
γ-AlO

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title = "Microwave-heated γ-Alumina Applied to the Reduction of Aldehydes to Alcohols",

abstract = "The development of cheap and robust heterogeneous catalysts for the Meerwein-Ponndorf-Verley (MPV) reduction is desirable due to the difficulties in product isolation and catalyst recovery associated with the traditional use of homogeneous catalysts for MPV. Herein, we show that microwave heated γ-Al2O3 can be used for the reduction of aldehydes to alcohols. The reaction is efficient and has a broad substrates scope (19 entries). The products can be isolated by simple filtration, and the catalyst can be regenerated. With the use of microwave heating, we can direct the heating to the catalyst rather than to the whole reaction medium. Furthermore, DFT was used to study the reaction mechanism, and we can conclude that a dual-site mechanism is operative where the aldehyde and 2-propoxide are situated on two adjacent Al sites during the reduction. Additionally, volcano plots were used to rationalize the reactivity of Al2O3 in comparison to other metal oxides.",

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AU - Dhokale, Bhausaheb

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AU - Pekkari, Anna

AU - Runemark, August

AU - Moth-Poulsen, Kasper

AU - Langhammer, Christoph

AU - Härelind, Hanna

AU - Busch, Michael

AU - Vandichel, Matthias

AU - Sundén, Henrik

PY - 2020/12/16

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N2 - The development of cheap and robust heterogeneous catalysts for the Meerwein-Ponndorf-Verley (MPV) reduction is desirable due to the difficulties in product isolation and catalyst recovery associated with the traditional use of homogeneous catalysts for MPV. Herein, we show that microwave heated γ-Al2O3 can be used for the reduction of aldehydes to alcohols. The reaction is efficient and has a broad substrates scope (19 entries). The products can be isolated by simple filtration, and the catalyst can be regenerated. With the use of microwave heating, we can direct the heating to the catalyst rather than to the whole reaction medium. Furthermore, DFT was used to study the reaction mechanism, and we can conclude that a dual-site mechanism is operative where the aldehyde and 2-propoxide are situated on two adjacent Al sites during the reduction. Additionally, volcano plots were used to rationalize the reactivity of Al2O3 in comparison to other metal oxides.

AB - The development of cheap and robust heterogeneous catalysts for the Meerwein-Ponndorf-Verley (MPV) reduction is desirable due to the difficulties in product isolation and catalyst recovery associated with the traditional use of homogeneous catalysts for MPV. Herein, we show that microwave heated γ-Al2O3 can be used for the reduction of aldehydes to alcohols. The reaction is efficient and has a broad substrates scope (19 entries). The products can be isolated by simple filtration, and the catalyst can be regenerated. With the use of microwave heating, we can direct the heating to the catalyst rather than to the whole reaction medium. Furthermore, DFT was used to study the reaction mechanism, and we can conclude that a dual-site mechanism is operative where the aldehyde and 2-propoxide are situated on two adjacent Al sites during the reduction. Additionally, volcano plots were used to rationalize the reactivity of Al2O3 in comparison to other metal oxides.

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Microwave-heated γ-Alumina Applied to the Reduction of Aldehydes to Alcohols

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Keywords

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