Literature DB >> 24687770

Reactions of nucleophiles with nitroarenes: multifacial and versatile electrophiles.

Mieczysław Mąkosza1.   

Abstract

In this overview, it is shown that there are many initial reactions between nitroarenes and nucleophiles: addition to the electron-deficient ring at positions occupied by halogen and hydrogen atoms, addition to the nitro group, single-electron transfer (SET), and other types of initial reactions. The resulting intermediates react further in a variety of ways to form products of nucleophilic substitution of a halogen atom (SN Ar), a hydrogen atom (SN ArH), and others. Many variants of these processes are briefly discussed, particularly in relation of rates of the initial reactions and further transformations.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbanions; nitroarenes; oxidation; single-electron transfer; vicarious nucleophilic substitution

Year:  2014        PMID: 24687770     DOI: 10.1002/chem.201400097

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  9 in total

1.  Corrole and nucleophilic aromatic substitution are not incompatible: a novel route to 2,3-difunctionalized copper corrolates.

Authors:  M Stefanelli; F Mandoj; S Nardis; M Raggio; F R Fronczek; G T McCandless; K M Smith; R Paolesse
Journal:  Org Biomol Chem       Date:  2015-05-19       Impact factor: 3.876

2.  Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds.

Authors:  Hongyin Gao; Zhe Zhou; Doo-Hyun Kwon; James Coombs; Steven Jones; Nicole Erin Behnke; Daniel H Ess; László Kürti
Journal:  Nat Chem       Date:  2016-11-28       Impact factor: 24.427

3.  Gas-Phase Anionic σ-Adduct (Trans)formations in Heteroaromatic Systems.

Authors:  Magdalena Zimnicka; Witold Danikiewicz
Journal:  J Am Soc Mass Spectrom       Date:  2015-04-21       Impact factor: 3.109

4.  General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C-H acids in aprotic media promoted by combination of strong bases and silylating agents.

Authors:  Michał Wiȩcław; Mariusz Bobin; Andrzej Kwast; Robert Bujok; Zbigniew Wróbel; Krzysztof Wojciechowski
Journal:  Mol Divers       Date:  2015-08-11       Impact factor: 2.943

5.  Construction of highly functionalized carbazoles via condensation of an enolate to a nitro group.

Authors:  Tej Narayan Poudel; Yong Rok Lee
Journal:  Chem Sci       Date:  2015-09-16       Impact factor: 9.825

6.  Transition metal-free direct dehydrogenative arylation of activated C(sp3)-H bonds: synthetic ambit and DFT reactivity predictions.

Authors:  Kaitlyn Lovato; Lirong Guo; Qing-Long Xu; Fengting Liu; Muhammed Yousufuddin; Daniel H Ess; László Kürti; Hongyin Gao
Journal:  Chem Sci       Date:  2018-08-27       Impact factor: 9.825

7.  Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines.

Authors:  Maxim A Bastrakov; Alexey K Fedorenko; Alexey M Starosotnikov; Ivan V Fedyanin; Vladimir A Kokorekin
Journal:  Molecules       Date:  2020-05-08       Impact factor: 4.411

8.  How Do Aromatic Nitro Compounds React with Nucleophiles? Theoretical Description Using Aromaticity, Nucleophilicity and Electrophilicity Indices.

Authors:  Kacper Błaziak; Witold Danikiewicz; Mieczysław Mąkosza
Journal:  Molecules       Date:  2020-10-20       Impact factor: 4.411

9.  A Walk through Recent Nitro Chemistry Advances.

Authors:  Nagatoshi Nishiwaki
Journal:  Molecules       Date:  2020-08-12       Impact factor: 4.411

  9 in total

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