Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids

Huanhuan Li, Sabry H.H. Younes, Shaohang Chen, Peigao Duan*, Chengsen Cui, Ron Wever, Wuyuan Zhang, Frank Hollmann

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)
46 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)4554-4559
JournalACS Catalysis
Volume12
Issue number8
DOIs
Publication statusPublished - 2022

Keywords

  • biocatalysis
  • decarboxylation
  • Hunsdiecker reaction
  • unsaturated carboxylic acids
  • vanadium chloroperoxidase
  • vinyl bromides

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