Issue 1, 2021
From the journal:

Organic Chemistry Frontiers

Oxidative nucleophilic alkoxylation of nitrobenzenes†

Viktor V. Khutorianskyi, ORCID logo a   Norbert Baris ORCID logo a  and  Petr Beier ORCID logo *a  

* Corresponding authors

a Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo náměstí 2, 166 10 Prague 6, Czech Republic
E-mail: beier@uochb.cas.cz

Abstract

Oxidative nucleophilic aromatic substitution of hydrogen in nitroaromatics with potassium alkoxides derived from primary, secondary or tertiary alcohols in the presence of oxygen was achieved. Mechanistic investigations suggest the formation of a deprotonated σH adduct. The products showed good reactivity in nucleophilic aromatic substitution of the nitro group with oxygen or nitrogen nucleophiles to access selectively substituted aromatic compounds.

Graphical abstract: Oxidative nucleophilic alkoxylation of nitrobenzenes

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Article information

DOI
https://doi.org/10.1039/D0QO01291B
Article type
Research Article
Submitted
20 Oct 2020
Accepted
04 Nov 2020
First published
05 Nov 2020

Org. Chem. Front., 2021,8, 77-81

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Oxidative nucleophilic alkoxylation of nitrobenzenes

V. V. Khutorianskyi, N. Baris and P. Beier, Org. Chem. Front., 2021, 8, 77 DOI: 10.1039/D0QO01291B

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