Electrochemical-Induced Cascade Reaction of 2-Formyl Benzonitrile with Anilines: Synthesis of N-Aryl Isoindolinones

An electrochemical initiated tandem reaction of anilines with 2-formyl benzonitrile has been developed. Thus, unprecedented 3-N-aryl substituted isoindolinones have been conveniently achieved by constant current electrolysis in a divided cell using catalytic amount of electricity and supporting elec...

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Autores principales: Morlacci, Valerio, Caruso, Tonino, Chiarini, Marco, Arcadi, Antonio, Aschi, Massimiliano, Palombi, Laura
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9738245/
https://www.ncbi.nlm.nih.gov/pubmed/36500288
http://dx.doi.org/10.3390/molecules27238199
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author Morlacci, Valerio
Caruso, Tonino
Chiarini, Marco
Arcadi, Antonio
Aschi, Massimiliano
Palombi, Laura
author_facet Morlacci, Valerio
Caruso, Tonino
Chiarini, Marco
Arcadi, Antonio
Aschi, Massimiliano
Palombi, Laura
author_sort Morlacci, Valerio
collection PubMed
description An electrochemical initiated tandem reaction of anilines with 2-formyl benzonitrile has been developed. Thus, unprecedented 3-N-aryl substituted isoindolinones have been conveniently achieved by constant current electrolysis in a divided cell using catalytic amount of electricity and supporting electrolyte and a Pt-cathode as working electrode. The origin of the electrochemical activation as well as the mechanism of the subsequent chemical cascade reactions have been investigated by DFT calculations.
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spelling pubmed-97382452022-12-11 Electrochemical-Induced Cascade Reaction of 2-Formyl Benzonitrile with Anilines: Synthesis of N-Aryl Isoindolinones Morlacci, Valerio Caruso, Tonino Chiarini, Marco Arcadi, Antonio Aschi, Massimiliano Palombi, Laura Molecules Article An electrochemical initiated tandem reaction of anilines with 2-formyl benzonitrile has been developed. Thus, unprecedented 3-N-aryl substituted isoindolinones have been conveniently achieved by constant current electrolysis in a divided cell using catalytic amount of electricity and supporting electrolyte and a Pt-cathode as working electrode. The origin of the electrochemical activation as well as the mechanism of the subsequent chemical cascade reactions have been investigated by DFT calculations. MDPI 2022-11-24 /pmc/articles/PMC9738245/ /pubmed/36500288 http://dx.doi.org/10.3390/molecules27238199 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Morlacci, Valerio
Caruso, Tonino
Chiarini, Marco
Arcadi, Antonio
Aschi, Massimiliano
Palombi, Laura
Electrochemical-Induced Cascade Reaction of 2-Formyl Benzonitrile with Anilines: Synthesis of N-Aryl Isoindolinones
title Electrochemical-Induced Cascade Reaction of 2-Formyl Benzonitrile with Anilines: Synthesis of N-Aryl Isoindolinones
title_full Electrochemical-Induced Cascade Reaction of 2-Formyl Benzonitrile with Anilines: Synthesis of N-Aryl Isoindolinones
title_fullStr Electrochemical-Induced Cascade Reaction of 2-Formyl Benzonitrile with Anilines: Synthesis of N-Aryl Isoindolinones
title_full_unstemmed Electrochemical-Induced Cascade Reaction of 2-Formyl Benzonitrile with Anilines: Synthesis of N-Aryl Isoindolinones
title_short Electrochemical-Induced Cascade Reaction of 2-Formyl Benzonitrile with Anilines: Synthesis of N-Aryl Isoindolinones
title_sort electrochemical-induced cascade reaction of 2-formyl benzonitrile with anilines: synthesis of n-aryl isoindolinones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9738245/
https://www.ncbi.nlm.nih.gov/pubmed/36500288
http://dx.doi.org/10.3390/molecules27238199
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