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