A chemo-enzymatic tandem reaction in a mixture of deep eutectic solvent and water in continuous flow

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Abstract

The combination of metal- and biocatalysis is a challenging but forward-looking topic in synthetic chemistry. The unique selectivity of enzymes paired with the broad range of applications of chemical catalysts enables an undreamed-of number of novel processes. Herein, we describe the application of immobilized phenolic acid decarboxylase (PAD) for the decarboxylation of para coumaric acid and subsequent Pd-catalyzed Heck cross coupling with an aryl halide in a fully integrated two-step continuous flow process to synthesize (E) 4 hydroxy-stilbene. The application of a choline chloride based deep eutectic solvent (DES) proved to be crucial to overcome the problem of solvent compatibility and enabled an increase in substrate concentration (from 5 mM in buffer to 20 mM in DES) as well as a process with a homogeneous starting solution. The two-step process was successfully operated for more than 16 h in continuous flow and full conversion was achieved. The results underline the usefulness of DES to overcome compatibility problems in tandem-catalytic processes. The system benefits from its simplicity due to increased substrate solubility, the possibility to conduct both reactions at their optimal temperatures and the elimination of isolating the reaction intermediate, which is prone to polymerization.
Original languageEnglish
Pages (from-to)263-269
JournalReaction Chemistry & Engineering
Volume5
Issue number2
DOIs
Publication statusPublished - 2020

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Eutectics
Water
Stilbenes
Reaction intermediates
Acids
Catalyst selectivity
Substrates
Choline
Buffers
Enzymes
Solubility
Metals
Polymerization
Catalysts
Temperature

Cite this

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title = "A chemo-enzymatic tandem reaction in a mixture of deep eutectic solvent and water in continuous flow",
abstract = "The combination of metal- and biocatalysis is a challenging but forward-looking topic in synthetic chemistry. The unique selectivity of enzymes paired with the broad range of applications of chemical catalysts enables an undreamed-of number of novel processes. Herein, we describe the application of immobilized phenolic acid decarboxylase (PAD) for the decarboxylation of para coumaric acid and subsequent Pd-catalyzed Heck cross coupling with an aryl halide in a fully integrated two-step continuous flow process to synthesize (E) 4 hydroxy-stilbene. The application of a choline chloride based deep eutectic solvent (DES) proved to be crucial to overcome the problem of solvent compatibility and enabled an increase in substrate concentration (from 5 mM in buffer to 20 mM in DES) as well as a process with a homogeneous starting solution. The two-step process was successfully operated for more than 16 h in continuous flow and full conversion was achieved. The results underline the usefulness of DES to overcome compatibility problems in tandem-catalytic processes. The system benefits from its simplicity due to increased substrate solubility, the possibility to conduct both reactions at their optimal temperatures and the elimination of isolating the reaction intermediate, which is prone to polymerization.",
author = "Bianca Grabner and Schweiger, {Anna Katharina} and Kristian Gavric and Robert Kourist and Heidrun Gruber-W{\"o}lfler",
year = "2020",
doi = "10.1039/C9RE00467J",
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pages = "263--269",
journal = "Reaction Chemistry & Engineering",
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T1 - A chemo-enzymatic tandem reaction in a mixture of deep eutectic solvent and water in continuous flow

AU - Grabner, Bianca

AU - Schweiger, Anna Katharina

AU - Gavric, Kristian

AU - Kourist, Robert

AU - Gruber-Wölfler, Heidrun

PY - 2020

Y1 - 2020

N2 - The combination of metal- and biocatalysis is a challenging but forward-looking topic in synthetic chemistry. The unique selectivity of enzymes paired with the broad range of applications of chemical catalysts enables an undreamed-of number of novel processes. Herein, we describe the application of immobilized phenolic acid decarboxylase (PAD) for the decarboxylation of para coumaric acid and subsequent Pd-catalyzed Heck cross coupling with an aryl halide in a fully integrated two-step continuous flow process to synthesize (E) 4 hydroxy-stilbene. The application of a choline chloride based deep eutectic solvent (DES) proved to be crucial to overcome the problem of solvent compatibility and enabled an increase in substrate concentration (from 5 mM in buffer to 20 mM in DES) as well as a process with a homogeneous starting solution. The two-step process was successfully operated for more than 16 h in continuous flow and full conversion was achieved. The results underline the usefulness of DES to overcome compatibility problems in tandem-catalytic processes. The system benefits from its simplicity due to increased substrate solubility, the possibility to conduct both reactions at their optimal temperatures and the elimination of isolating the reaction intermediate, which is prone to polymerization.

AB - The combination of metal- and biocatalysis is a challenging but forward-looking topic in synthetic chemistry. The unique selectivity of enzymes paired with the broad range of applications of chemical catalysts enables an undreamed-of number of novel processes. Herein, we describe the application of immobilized phenolic acid decarboxylase (PAD) for the decarboxylation of para coumaric acid and subsequent Pd-catalyzed Heck cross coupling with an aryl halide in a fully integrated two-step continuous flow process to synthesize (E) 4 hydroxy-stilbene. The application of a choline chloride based deep eutectic solvent (DES) proved to be crucial to overcome the problem of solvent compatibility and enabled an increase in substrate concentration (from 5 mM in buffer to 20 mM in DES) as well as a process with a homogeneous starting solution. The two-step process was successfully operated for more than 16 h in continuous flow and full conversion was achieved. The results underline the usefulness of DES to overcome compatibility problems in tandem-catalytic processes. The system benefits from its simplicity due to increased substrate solubility, the possibility to conduct both reactions at their optimal temperatures and the elimination of isolating the reaction intermediate, which is prone to polymerization.

U2 - 10.1039/C9RE00467J

DO - 10.1039/C9RE00467J

M3 - Article

VL - 5

SP - 263

EP - 269

JO - Reaction Chemistry & Engineering

JF - Reaction Chemistry & Engineering

SN - 2058-9883

IS - 2

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