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Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids

Journal Article (2022)
Author(s)

Huanhuan Li (Chinese Academy of Sciences)

Sabry H.H. Younes (TU Delft - Applied Sciences, Sohag University)

Shaohang Chen (Chinese Academy of Sciences)

Peigao Duan (Xi’an Jiaotong University)

Chengsen Cui (Chinese Academy of Sciences, National Center of Technology Innovation for Synthetic Biology, Tianjin)

Ron Wever (Universiteit van Amsterdam)

Wuyuan Zhang (National Center of Technology Innovation for Synthetic Biology, Tianjin, Chinese Academy of Sciences)

Frank Hollmann (TU Delft - Applied Sciences)

Research Group
BT/Biocatalysis
DOI related publication
https://doi.org/10.1021/acscatal.2c00485 Final published version
More Info
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Publication Year
2022
Language
English
Research Group
BT/Biocatalysis
Issue number
8
Volume number
12
Pages (from-to)
4554-4559
Downloads counter
468
Collections
Institutional Repository
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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.