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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/14/5555 |
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| author | Letizia Sorti Fiammetta Vitulano Elia Cappellini Fulvio Uggeri Carlo Francesco Morelli Guido Sello Alessandro Minguzzi Alberto Vertova |
| author_facet | Letizia Sorti Fiammetta Vitulano Elia Cappellini Fulvio Uggeri Carlo Francesco Morelli Guido Sello Alessandro Minguzzi Alberto Vertova |
| author_sort | Letizia Sorti |
| collection | DOAJ |
| 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<sub>2</sub> and iodonium species. |
| first_indexed | 2024-03-11T00:47:05Z |
| format | Article |
| id | doaj.art-959a9567efc345989a54912bda2b28dd |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T00:47:05Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-959a9567efc345989a54912bda2b28dd2023-11-18T20:43:49ZengMDPI AGMolecules1420-30492023-07-012814555510.3390/molecules28145555Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green ApproachLetizia Sorti0Fiammetta Vitulano1Elia Cappellini2Fulvio Uggeri3Carlo Francesco Morelli4Guido Sello5Alessandro Minguzzi6Alberto Vertova7Laboratory of Applied Electrochemistry, Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi, 19, 20133 Milano, ItalyLaboratory of Applied Electrochemistry, Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi, 19, 20133 Milano, ItalyLaboratory of Applied Electrochemistry, Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi, 19, 20133 Milano, ItalyBracco SpA, Via Caduti di Marcinelle, 13, 20134 Milano, ItalyLaboratory of Applied Electrochemistry, Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi, 19, 20133 Milano, ItalyLaboratory of Applied Electrochemistry, Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi, 19, 20133 Milano, ItalyLaboratory of Applied Electrochemistry, Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi, 19, 20133 Milano, ItalyLaboratory of Applied Electrochemistry, Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi, 19, 20133 Milano, ItalyThe 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<sub>2</sub> and iodonium species.https://www.mdpi.com/1420-3049/28/14/5555electro-organic synthesisgreen chemistryiodination reactions5-hydroxyisophthalic acid iodination5-sulfosalicylic acid iodinationelectrosynthesis in aqueous solvent |
| spellingShingle | Letizia Sorti Fiammetta Vitulano Elia Cappellini Fulvio Uggeri Carlo Francesco Morelli Guido Sello Alessandro Minguzzi Alberto Vertova Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green Approach Molecules electro-organic synthesis green chemistry iodination reactions 5-hydroxyisophthalic acid iodination 5-sulfosalicylic acid iodination electrosynthesis in aqueous solvent |
| 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 | electro-organic synthesis green chemistry iodination reactions 5-hydroxyisophthalic acid iodination 5-sulfosalicylic acid iodination electrosynthesis in aqueous solvent |
| url | https://www.mdpi.com/1420-3049/28/14/5555 |
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