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Authors: Gombos, Lilla G.
Werner, Leo
Schollmeyer, Dieter
Martínez-Huitle, Carlos A.
Waldvogel, Siegfried R.
Title: Selective electrochemical dibromination of terpenes and naturally derived olefins
Online publication date: 30-Jan-2023
Year of first publication: 2022
Language: english
Abstract: A simple electrochemical protocol is established for the selective alkene dibromination of naturally derived olefins, such as terpenes. The use of hazardous Br2 or its analogues have been elegantly avoided by employing readily available, inexpensive, and harmless sodium bromide with a dual role as reagent and supporting electrolyte in combination with sustainable carbon-based electrodes. This electrochemical protocol provides the desired products with good to excellent yields up to 82 % with 10 examples. Scalability has been proved by a 5-fold scale-up. Notably, higher yields and selectivity were achieved in comparison to conventional bromination by Br2 and DMSO/HBr system and the dibrominated compound was eligible for further functionalization, such as cyanation according to the Kolbe nitrile synthesis protocol.
DDC: 540 Chemie
540 Chemistry and allied sciences
Institution: Johannes Gutenberg-Universität Mainz
Department: FB 09 Chemie, Pharmazie u. Geowissensch.
Place: Mainz
Version: Published version
Publication type: Zeitschriftenaufsatz
License: CC BY-NC-ND
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Journal: European journal of organic chemistry
Pages or article number: e202200857
Publisher: Wiley VCZ
Publisher place: Weinheim
Issue date: 2022
ISSN: 1099-0690
Publisher DOI: 10.1002/ejoc.202200857
Appears in collections:DFG-491381577-H

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