Optimization of a Catalytic Chemoenzymatic Tandem Reaction for the Synthesis of Natural Stilbenes in Continuous Flow

In view of the development of efficient processes for the synthesis of high-value compounds, the combination of bio- and chemocatalysis is highly promising. In addition, implementation of immobilized catalysts into continuous setups allows a straightforward separation of the target compound from the...

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Bibliographic Details
Published in:Catalysts 2020-12, Vol.10 (12), p.1404
Main Authors: Lackner, Florian, Hiebler, Katharina, Grabner, Bianca, Gruber-Woelfler, Heidrun
Format: Article
Language:English
Subjects:
Aromatic compounds
Cascade chemical reactions
catalysis
catalyst leaching
Catalysts
Chemical reactions
Chemical synthesis
chemoenzymatic tandem
Continuous flow
continuous flow chemistry
Cross coupling
Decarboxylation
Design of experiments
Fixed bed reactors
Heck reaction
Leaching
Optimization
Packed beds
Palladium
Phenolic acids
Process controls
Reversed flow
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Summary:In view of the development of efficient processes for the synthesis of high-value compounds, the combination of bio- and chemocatalysis is highly promising. In addition, implementation of immobilized catalysts into continuous setups allows a straightforward separation of the target compound from the reaction mixture and ensures uniform product quality. In this work, we report the optimization of a chemoenzymatic tandem reaction in continuous flow and its extended application for the synthesis of pharmacologically active resveratrol and pterostilbene. The tandem reaction involves enzymatic decarboxylation of coumaric acid employing encapsulated phenolic acid decarboxylase from B. subtilis and a Heck coupling of the obtained vinylphenol with an aryl iodide using heterogeneous Pd-Ce-Sn oxides implemented in a packed bed reactor. By optimization of the reaction conditions for the limiting cross-coupling step, the yield of (E)-4-hydroxystilbene using the fully continuous setup could be more than doubled compared to previous work. Furthermore, the improved chemoenzymatic cascade could also be applied to the synthesis of resveratrol and pterostilbene in a continuous fashion. Leaching of the metal catalyst at high temperatures limited the process in many perspectives. Therefore, the feasibility of a reactor setup with reversed flow was experimentally evaluated and approved.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal10121404