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

doi:10.1021/acscatal.2c00485

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

化学工程与技术学院

Xi'an Jiaotong University
CAS - Tianjin Institute of Industrial Biotechnology
Delft University of Technology
Sohag University
National Technology Innovation Center of Synthetic Biology
University of Amsterdam

科研成果: 期刊稿件 › 文章 › 同行评审

27 引用（Scopus）

摘要

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 H₂O₂and 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.

源语言	英语
页（从-至）	4554-4559
页数	6
期刊	ACS Catalysis
卷	12
期	8
DOI	https://doi.org/10.1021/acscatal.2c00485
出版状态	已出版 - 15 4月 2022

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10.1021/acscatal.2c00485

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title = "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 H2O2and 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.",

keywords = "Hunsdiecker reaction, biocatalysis, decarboxylation, unsaturated carboxylic acids, vanadium chloroperoxidase, vinyl bromides",

author = "Huanhuan Li and Younes, \{Sabry H.H.\} and Shaohang Chen and Peigao Duan and Chengsen Cui and Ron Wever and Wuyuan Zhang and Frank Hollmann",

year = "2022",

month = apr,

day = "15",

doi = "10.1021/acscatal.2c00485",

language = "英语",

volume = "12",

pages = "4554--4559",

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}

TY - JOUR

T1 - Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids

AU - Li, Huanhuan

AU - Younes, Sabry H.H.

AU - Chen, Shaohang

AU - Duan, Peigao

AU - Cui, Chengsen

AU - Wever, Ron

AU - Zhang, Wuyuan

AU - Hollmann, Frank

PY - 2022/4/15

Y1 - 2022/4/15

N2 - 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 H2O2and 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.

AB - 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 H2O2and 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.

KW - Hunsdiecker reaction

KW - biocatalysis

KW - decarboxylation

KW - unsaturated carboxylic acids

KW - vanadium chloroperoxidase

KW - vinyl bromides

UR - https://www.scopus.com/pages/publications/85128216059

U2 - 10.1021/acscatal.2c00485

DO - 10.1021/acscatal.2c00485

M3 - 文章

AN - SCOPUS:85128216059

SN - 2155-5435

VL - 12

SP - 4554

EP - 4559

JO - ACS Catalysis

JF - ACS Catalysis

IS - 8

ER -

Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids

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