Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids

Journal article (2022)

Authors

Huanhuan Li Chinese Academy of Sciences
S.H.H. Younes BT/Biocatalysis - AS , Sohag University
Shaohang Chen Chinese Academy of Sciences
Peigao Duan Xi’an Jiaotong University
Chengsen Cui National Center of Technology Innovation for Synthetic Biology, Tianjin, Chinese Academy of Sciences
Ron Wever Universiteit van Amsterdam
Wuyuan Zhang Chinese Academy of Sciences, National Center of Technology Innovation for Synthetic Biology, Tianjin
F. Hollmann BT/Biocatalysis - AS
Research Group
BT/Biocatalysis (AS) (TU Delft)
Copyright: © 2022 Huanhuan Li, S.H.H. Younes, Shaohang Chen, Peigao Duan, Chengsen Cui, Ron Wever, Wuyuan Zhang, F. Hollmann
DOI
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https://doi.org/10.1021/acscatal.2c00485
Biocatalysis Decarboxylation Vanadium chloroperoxidase Hunsdiecker reaction Unsaturated carboxylic acids Vinyl bromides
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Published Date

2022

Language

English

Faculty

Applied Sciences

Department

BT/Biotechnologie

Research Group

BT/Biocatalysis

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.