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Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry

Hiebler, Katharina; Lichtenegger, Georg J.; Maier, Manuel C.; Park, Eun Sung; Gonzales-Groom, Renie; Binks, Bernard P.; Gruber-Woelfler, Heidrun

Authors

Katharina Hiebler

Georg J. Lichtenegger

Manuel C. Maier

Eun Sung Park

Renie Gonzales-Groom

Heidrun Gruber-Woelfler

Abstract

Within the “Compartmentalised Smart Factory” approach of the ONE-FLOW project the implementation of different catalysts in “compartments” provided by Pickering emulsions and their application in continuous flow is targeted. We present here the development of heterogeneous Pd-catalysts that are ready to be used in combination with biocatalysts for catalytic cascade syntheses of active pharmaceutical ingredients (APIs). In particular, we focus on the application of the catalytic systems for Suzuki-Miyaura cross coupling reactions, which is the key step in the syntheses of the targeted APIs valsartan and sacubitril. An immobilised enzyme will accomplish the final product formation via hydrolysis. In order to create large interfacial area for the catalytic reactions and to keep the reagents separated until required, the catalyst particles are used to stabilise Pickering emulsions of oil and water. A set of Ce-Sn-Pd-oxides with the molecular formula Ce0.99-xSnxPd0.01O2-(x= 0-0.99) has been prepared utilising a simple single-step solution combustion method. The high applicability of the catalysts for different functional groups and their minimal leaching behaviour is demonstrated with various Suzuki-Miyaura cross coupling reactions in batch as well as in continuous flow employing the so-called “Plug & Play reactor”. Finally, we demonstrate the use of these particles as the sole emulsifier of oil + water emulsions for a range of oils.

Journal Article Type Article
Publication Date Mar 19, 2018
Print ISSN 1860-5397
Electronic ISSN 1860-5397
Publisher Beilstein-Institut
Peer Reviewed Peer Reviewed
Volume 14
Pages 648-658
Institution Citation Hiebler, K., Lichtenegger, G. J., Maier, M. C., Park, E. S., Gonzales-Groom, R., Binks, B. P., & Gruber-Woelfler, H. (2018). Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry. Beilstein Journal of Organic Chemistry, 14, 648-658. https://doi.org/10.3762/bjoc.14.52
DOI https://doi.org/10.3762/bjoc.14.52
Keywords Compartmentalisation; Heterogeneous catalysis; Multistep flow chemistry; Palladium; Pickering emulsions
Publisher URL https://www.beilstein-journals.org/bjoc/articles/14/52
Copyright Statement © 2018 The authors; licensee Beilstein-Institut.
This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc)

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