Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids

Li, Huanhuan; Younes, S.H.H.; Chen, Shaohang; Duan, Peigao; Cui, Chengsen; Wever, Ron; Zhang, Wuyuan; Hollmann, F.

doi:10.1021/acscatal.2c00485

Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids

Title

Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids

Author

Li, Huanhuan (Chinese Academy of Sciences)
Younes, S.H.H. (TU Delft BT/Biocatalysis; Sohag University)
Chen, Shaohang (Chinese Academy of Sciences)
Duan, Peigao (Xi’an Jiaotong University)
Cui, Chengsen (Chinese Academy of Sciences; National Center of Technology Innovation for Synthetic Biology, Tianjin)
Wever, Ron (Universiteit van Amsterdam)
Zhang, Wuyuan (Chinese Academy of Sciences; National Center of Technology Innovation for Synthetic Biology, Tianjin)
Hollmann, F. (TU Delft BT/Biocatalysis)

Date

2022

Abstract

In this contribution, we report chemoenzymatic bromodecarboxylation (Hunsdiecker-type) of α,ß-unsaturated carboxylic acids. The extraordinarily robust chloroperoxidase from Curvularia inaequalis (CiVCPO) generated hypobromite from H2O2 and bromide, which then spontaneously reacted with a broad range of unsaturated carboxylic acids and yielded the corresponding vinyl bromide products. Selectivity issues arising from the (here undesired) addition of water to the intermediate bromonium ion could be solved by reaction medium engineering. The vinyl bromides so obtained could be used as starting materials for a range of cross-coupling and pericyclic reactions.

Subject

biocatalysis
decarboxylation
Hunsdiecker reaction
unsaturated carboxylic acids
vanadium chloroperoxidase
vinyl bromides

To reference this document use:

http://resolver.tudelft.nl/uuid:405f342d-f901-4259-ac5b-bbef8c023161

DOI

https://doi.org/10.1021/acscatal.2c00485

ISSN

2155-5435

Source

ACS Catalysis, 12 (8), 4554-4559

Part of collection

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