Please use this identifier to cite or link to this item:
http://doi.org/10.25358/openscience-8695
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 |
ROR: | https://ror.org/023b0x485 |
DOI: | http://doi.org/10.25358/openscience-8695 |
Version: | Published version |
Publication type: | Zeitschriftenaufsatz |
License: | CC BY-NC-ND |
Information on rights of use: | https://creativecommons.org/licenses/by-nc-nd/4.0/ |
Journal: | European journal of organic chemistry 2022 47 |
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 |
Files in This Item:
File | Description | Size | Format | ||
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![]() | selective_electrochemical_dib-20230130110343444.pdf | 4.01 MB | Adobe PDF | View/Open |