Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids
Huanhuan Li (Chinese Academy of Sciences)
Sabry H H Younes (TU Delft - BT/Biocatalysis, 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 - BT/Biocatalysis)
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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.
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