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Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids.

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.

SUBMITTER: Li H

PROVIDER: S-EPMC9016706 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids.

Li Huanhuan H Younes Sabry H H SHH Chen Shaohang S Duan Peigao P Cui Chengsen C Wever Ron R Zhang Wuyuan W Hollmann Frank F

ACS catalysis 20220404 8

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 ...[more]

PMID: 35465241

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