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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
Version: Published version
Publication type: Zeitschriftenaufsatz
License: CC BY-NC-ND
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Journal: ChemSusChem
Pages or article number: 4936
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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