Optimization of a catalytic chemoenzymatic tandem reaction for the synthesis of natural stilbenes in continuous flow

Florian Lackner, Katharina Hiebler, Bianca Grabner, Heidrun Gruber-Woelfler*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish
Article number1404
Pages (from-to)1-13
Number of pages13
Issue number12
Publication statusPublished - Dec 2020


  • Catalysis
  • Catalyst leaching
  • Chemoenzymatic tandem
  • Continuous flow chemistry
  • Decarboxylation
  • Heck reaction
  • Optimization
  • Palladium
  • Stilbenes

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry


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