A chemo-enzymatic tandem reaction in a mixture of deep eutectic solvent and water in continuous flow,Reaction Chemistry & Engineering

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A chemo-enzymatic tandem reaction in a mixture of deep eutectic solvent and water in continuous flow
Reaction Chemistry & Engineering ( IF 3.4 ) Pub Date : 2020/01/03 , DOI: 10.1039/c9re00467j
Bianca Grabner _{1,

2,

3,

4} , Anna K. Schweiger _{2,

3,

4,

5} , Kristian Gavric _{1,

2,

3,

4} , Robert Kourist _{2,

3,

4,

5} , Heidrun Gruber-Woelfler _{1,

2,

3,

4}

Affiliation

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.

中文翻译：

在深流共熔溶剂和水的混合物中进行化学-酶促串联反应

金属催化和生物催化的结合是合成化学中具有挑战性但具有前瞻性的主题。酶的独特选择性与化学催化剂的广泛应用相结合，实现了数量众多的新颖工艺。在本文中，我们描述了固定化的酚酸脱羧酶（PAD）在对-香豆酸脱羧以及随后Pd催化的Heck与芳基卤化物的偶联在完全集成的两步连续流动过程中合成的应用（E）-4-羟基-sti。事实证明，应用基于氯化胆碱的深共熔溶剂（DES）对于解决溶剂相容性问题至关重要，并且能够提高底物浓度（从缓冲液中的5 mM到DES中的20 mM），以及使用均匀的起始溶液。两步法连续流操作成功超过16小时，并实现了完全转化。结果强调了DES在克服串联催化过程中的相容性问题方面的有用性。由于底物溶解度的提高，该系统的简单性，在最佳温度下进行两个反应的可能性以及消除了易于聚合的反应中间体的分离，使该系统受益。

更新日期：2020-02-13

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