Chemoenzymatic intermolecular haloether synthesis

Shaohang Chen; Jiaan Zhang; Zhigang Zeng; Zongjie Dai; Qinhong Wang; Ron Wever; Frank Hollmann; Wuyuan Zhang

doi:10.1016/j.mcat.2021.112061

Chemoenzymatic intermolecular haloether synthesis

Shaohang Chen, Jiaan Zhang, Zhigang Zeng^*, Zongjie Dai, Qinhong Wang, Ron Wever, Frank Hollmann, Wuyuan Zhang

^*Corresponding author for this work

BT/Biocatalysis

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Abstract

A chemoenzymatic method for the synthesis of haloethers is presented. A combination of enzymatic hypohalite synthesis with spontaneous oxidation of alkenes and nucleophilic attack by various alcohols enabled the synthesis of a wide range of haloethers. The reaction system has been characterised and current imitations have been worked out. In the present, aqueous reaction system, hydroxyhalide formation represents the main undesired side reaction. Nevertheless, semi-preparative scale synthesis of a range of haloethers is demonstrated.

Original language	English
Article number	112061
Number of pages	6
Journal	Molecular Catalysis
Volume	517
DOIs	https://doi.org/10.1016/j.mcat.2021.112061
Publication status	Published - 2022

Keywords

Chemoenzymatic synthesis
Ether synthesis
Haloetherification
Vanadium chloroperoxidase

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10.1016/j.mcat.2021.112061

1-s2.0-S2468823121006775-mainFinal published version, 1.02 MBLicence: CC BY

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title = "Chemoenzymatic intermolecular haloether synthesis",

abstract = "A chemoenzymatic method for the synthesis of haloethers is presented. A combination of enzymatic hypohalite synthesis with spontaneous oxidation of alkenes and nucleophilic attack by various alcohols enabled the synthesis of a wide range of haloethers. The reaction system has been characterised and current imitations have been worked out. In the present, aqueous reaction system, hydroxyhalide formation represents the main undesired side reaction. Nevertheless, semi-preparative scale synthesis of a range of haloethers is demonstrated.",

keywords = "Chemoenzymatic synthesis, Ether synthesis, Haloetherification, Vanadium chloroperoxidase",

author = "Shaohang Chen and Jiaan Zhang and Zhigang Zeng and Zongjie Dai and Qinhong Wang and Ron Wever and Frank Hollmann and Wuyuan Zhang",

year = "2022",

doi = "10.1016/j.mcat.2021.112061",

language = "English",

volume = "517",

journal = "Molecular Catalysis",

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TY - JOUR

T1 - Chemoenzymatic intermolecular haloether synthesis

AU - Chen, Shaohang

AU - Zhang, Jiaan

AU - Zeng, Zhigang

AU - Dai, Zongjie

AU - Wang, Qinhong

AU - Wever, Ron

AU - Hollmann, Frank

AU - Zhang, Wuyuan

PY - 2022

Y1 - 2022

N2 - A chemoenzymatic method for the synthesis of haloethers is presented. A combination of enzymatic hypohalite synthesis with spontaneous oxidation of alkenes and nucleophilic attack by various alcohols enabled the synthesis of a wide range of haloethers. The reaction system has been characterised and current imitations have been worked out. In the present, aqueous reaction system, hydroxyhalide formation represents the main undesired side reaction. Nevertheless, semi-preparative scale synthesis of a range of haloethers is demonstrated.

AB - A chemoenzymatic method for the synthesis of haloethers is presented. A combination of enzymatic hypohalite synthesis with spontaneous oxidation of alkenes and nucleophilic attack by various alcohols enabled the synthesis of a wide range of haloethers. The reaction system has been characterised and current imitations have been worked out. In the present, aqueous reaction system, hydroxyhalide formation represents the main undesired side reaction. Nevertheless, semi-preparative scale synthesis of a range of haloethers is demonstrated.

KW - Chemoenzymatic synthesis

KW - Ether synthesis

KW - Haloetherification

KW - Vanadium chloroperoxidase

UR - http://www.scopus.com/inward/record.url?scp=85121313231&partnerID=8YFLogxK

U2 - 10.1016/j.mcat.2021.112061

DO - 10.1016/j.mcat.2021.112061

M3 - Article

AN - SCOPUS:85121313231

SN - 2468-8231

VL - 517

JO - Molecular Catalysis

JF - Molecular Catalysis

M1 - 112061

ER -

Chemoenzymatic intermolecular haloether synthesis

Abstract

Keywords

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