Please use this identifier to cite or link to this item:
http://doi.org/10.25358/openscience-8030
Authors: | Blum, Stephan P. Nickel, Christean Schäffer, Lukas Karakaya, Tarik Waldvogel, Siegfried R. |
Title: | Electrochemical nitration with nitrite |
Online publication date: | 25-Oct-2022 |
Year of first publication: | 2021 |
Language: | english |
Abstract: | Aromatic nitration has tremendous importance in organic chemistry as nitroaromatic compounds serve as versatile building blocks. This study represents the electrochemical aromatic nitration with NBu4NO2, which serves a dual role as supporting electrolyte and as a safe, readily available, and easy-to-handle nitro source. Stoichiometric amounts of 1,1,1-3,3,3-hexafluoroisopropan-2-ol (HFIP) in MeCN significantly increase the yield by solvent control. The reaction mechanism is based on electrochemical oxidation of nitrite to NO2, which initiates the nitration reaction in a divided electrolysis cell with inexpensive graphite electrodes. Overall, the reaction is demonstrated for 20 examples with yields of up to 88 %. Scalability is demonstrated by a 13-fold scale-up. |
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-8030 |
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: | ChemSusChem 14 22 |
Pages or article number: | 4936 4940 |
Publisher: | Wiley-VCH |
Publisher place: | Weinheim |
Issue date: | 2021 |
ISSN: | 1864-564X |
Publisher DOI: | 10.1002/cssc.202102053 |
Appears in collections: | JGU-Publikationen |
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