Please use this identifier to cite or link to this item:
http://doi.org/10.25358/openscience-9314
Authors: | Linden, Martin Hofmann, Silja Herman, Antonia Ehler, Nicole Bär, Robin M. Waldvogel, Siegfried R. |
Title: | Electrochemical synthesis of pyrazolines and pyrazoles via [3+2] dipolar cycloaddition |
Online publication date: | 3-Aug-2023 |
Year of first publication: | 2023 |
Language: | english |
Abstract: | Pyrazolines and pyrazoles are common and important motifs of pharmaceutical agents and agrochemicals. Herein, the first electrochemical approach for their direct synthesis from easily accessible hydrazones and dipolarophiles up to decagram scale is presented. The application of a biphasic system (aqueous/organic) even allows for the conversion of highly sensitive alkenes, wherein inexpensive sodium iodide is employed in a dual role as supporting electrolyte and mediator. In addition, mechanistic insight into the reaction is given by the isolation of key step intermediates. The relevance of the presented reaction is underlined by the synthesis of commercial herbicide safener mefenpyr-diethyl in good yields. |
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-9314 |
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: | Angewandte Chemie : international edition 62 9 |
Pages or article number: | e202214820 |
Publisher: | Wiley-VCH |
Publisher place: | Weinheim |
Issue date: | 2023 |
ISSN: | 1521-3773 |
Publisher DOI: | 10.1002/anie.202214820 |
Relations: | is version of 10.25358/openscience-10134 |
Appears in collections: | DFG-491381577-H |
Files in This Item:
File | Description | Size | Format | ||
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electrochemical_synthesis_of_-20230724162903803.pdf | 1.74 MB | Adobe PDF | View/Open |