Medium-dependent regioselectivity of electrochemical bromination of methyl levulinate

Dmitry A. Pirgach; Raghavendra Meena; Guanna Li; Fedor M. Miloserdov; Daan S. van Es; Pieter C. A. Bruijnincx; Johannes H. Bitter

doi:10.1039/d5su00037h

Medium-dependent regioselectivity of electrochemical bromination of methyl levulinate

Dmitry A. Pirgach, Raghavendra Meena, Guanna Li, Fedor M. Miloserdov, Daan S. van Es, Pieter C. A. Bruijnincx, Johannes H. Bitter^*

^*Corresponding author for this work

Sub Organic Chemistry and Catalysis

Wageningen University & Research

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

An electrochemical method for the bromination of renewable methyl levulinate using ammonium bromide is reported. Regioselectivity depended on the solvent used: the formation of 5-bromolevulinate was favored in methanol and 3-bromolevulinate in a MeCN : H2O mixture. To explain the observed change, different bromination mechanisms were proposed.

Original language	English
Pages (from-to)	2198-2204
Number of pages	7
Journal	Rsc Sustainability
Volume	3
Issue number	5
Early online date	7 Apr 2025
DOIs	https://doi.org/10.1039/d5su00037h
Publication status	Published - 1 May 2025

Bibliographical note

Publisher Copyright:
© 2025 RSC.

Funding

The authors gratefully acknowledge financial support from Wageningen University. Leane Gros is acknowledged for carrying out selected experiments.

Funders	Funder number
Wageningen University and Research

Keywords

5-aminolevulinic acid
Acetic-acid
Aromatic-compounds
Halogenation
Kinetics
Mechanism
Oxidation
Photodynamic therapy
Succinic acid
Water

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1039/d5su00037hLicence: CC BY

d5su00037hFinal published version, 525 KBLicence: CC BY

Cite this

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abstract = "An electrochemical method for the bromination of renewable methyl levulinate using ammonium bromide is reported. Regioselectivity depended on the solvent used: the formation of 5-bromolevulinate was favored in methanol and 3-bromolevulinate in a MeCN : H2O mixture. To explain the observed change, different bromination mechanisms were proposed.",

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AU - van Es, Daan S.

AU - Bruijnincx, Pieter C. A.

AU - Bitter, Johannes H.

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KW - Aromatic-compounds

KW - Halogenation

KW - Kinetics

KW - Mechanism

KW - Oxidation

KW - Photodynamic therapy

KW - Succinic acid

KW - Water

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Medium-dependent regioselectivity of electrochemical bromination of methyl levulinate

Abstract

Bibliographical note

Funding

Keywords

UN SDGs

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