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 I2 and iodonium species.

Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green Approach / L. Sorti, F. Vitulano, E. Cappellini, F. Uggeri, C. Morelli, G.G. Sello, A. Minguzzi, A. Vertova. - In: MOLECULES. - ISSN 1420-3049. - 28:14(2023), pp. 5555.1-5555.12. [10.3390/molecules28145555]

Electrochemical Iodination through the In Situ Generation of Iodinating Agents: A Promising Green Approach

L. Sorti
Primo
;
F. Vitulano
Secondo
;
C. Morelli;G.G. Sello;A. Minguzzi
Penultimo
;
A. Vertova
Ultimo
2023

Abstract

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 I2 and iodonium species.
electro-organic synthesis; green chemistry; iodination reactions; 5-hydroxyisophthalic acid iodination; 5-sulfosalicylic acid iodination; electrosynthesis in aqueous solvent
Settore CHIM/02 - Chimica Fisica
2023
https://susy.mdpi.com/user/manuscripts/review_info/b9c91ee69496e705f412aaa6a1323040
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/987708
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