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Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green Approach
The synthesis of iodinated compounds using cheap, simple, and green strategies is of fundamental importance. Iodination reactions are mainly used to synthesize useful intermediates, especially in the pharmaceutical field, where they are employed for the production of contrast media or of iodinated a...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10383702/ https://www.ncbi.nlm.nih.gov/pubmed/37513427 http://dx.doi.org/10.3390/molecules28145555 |
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author | Sorti, Letizia Vitulano, Fiammetta Cappellini, Elia Uggeri, Fulvio Morelli, Carlo Francesco Sello, Guido Minguzzi, Alessandro Vertova, Alberto |
author_facet | Sorti, Letizia Vitulano, Fiammetta Cappellini, Elia Uggeri, Fulvio Morelli, Carlo Francesco Sello, Guido Minguzzi, Alessandro Vertova, Alberto |
author_sort | Sorti, Letizia |
collection | PubMed |
description | The synthesis of iodinated compounds using cheap, simple, and green strategies is of fundamental importance. Iodination reactions are mainly used to synthesize useful intermediates, especially in the pharmaceutical field, where they are employed for the production of contrast media or of iodinated active pharmaceutical ingredients. Traditional synthetic methods suffer from the use of erosive, toxic, or hazardous reactants. Approaches which involve the use of molecular iodine as an iodinating agent require the addition of an oxidizing agent, which is often difficult to handle. Electrochemistry can offer a valid and green alternative by avoiding the addition of such oxidizing agents, transforming the iodine source in the active species through the use of electrons as the main reactants. Herein, we report the electrochemical iodination with the generation of iodinating species in situ in water by using iodides as the source of iodine atoms. First of all, the electrochemical behavior of iodide and iodine in water on carbonaceous anodes was studied and, after selecting the suitable potential, in situ electrochemical iodination was successfully applied to 5-hydroxyisophthalic acid and 5-sulfosalicylic acid, comparing the iodinating power of I(2) and iodonium species. |
format | Online Article Text |
id | pubmed-10383702 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-103837022023-07-30 Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green Approach Sorti, Letizia Vitulano, Fiammetta Cappellini, Elia Uggeri, Fulvio Morelli, Carlo Francesco Sello, Guido Minguzzi, Alessandro Vertova, Alberto Molecules Article The synthesis of iodinated compounds using cheap, simple, and green strategies is of fundamental importance. Iodination reactions are mainly used to synthesize useful intermediates, especially in the pharmaceutical field, where they are employed for the production of contrast media or of iodinated active pharmaceutical ingredients. Traditional synthetic methods suffer from the use of erosive, toxic, or hazardous reactants. Approaches which involve the use of molecular iodine as an iodinating agent require the addition of an oxidizing agent, which is often difficult to handle. Electrochemistry can offer a valid and green alternative by avoiding the addition of such oxidizing agents, transforming the iodine source in the active species through the use of electrons as the main reactants. Herein, we report the electrochemical iodination with the generation of iodinating species in situ in water by using iodides as the source of iodine atoms. First of all, the electrochemical behavior of iodide and iodine in water on carbonaceous anodes was studied and, after selecting the suitable potential, in situ electrochemical iodination was successfully applied to 5-hydroxyisophthalic acid and 5-sulfosalicylic acid, comparing the iodinating power of I(2) and iodonium species. MDPI 2023-07-20 /pmc/articles/PMC10383702/ /pubmed/37513427 http://dx.doi.org/10.3390/molecules28145555 Text en © 2023 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 Sorti, Letizia Vitulano, Fiammetta Cappellini, Elia Uggeri, Fulvio Morelli, Carlo Francesco Sello, Guido Minguzzi, Alessandro Vertova, Alberto Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green Approach |
title | Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green Approach |
title_full | Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green Approach |
title_fullStr | Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green Approach |
title_full_unstemmed | Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green Approach |
title_short | Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green Approach |
title_sort | electrochemical iodination through the in situ generation of iodinating agents: a promising green approach |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10383702/ https://www.ncbi.nlm.nih.gov/pubmed/37513427 http://dx.doi.org/10.3390/molecules28145555 |
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