Photocatalytic iodosulfonylation of internal alkynes under green conditions

A new "green" method for the synthesis of β-iodovinyl aryl and alkyl sulfones with high yield and selectivity has been developed. The reaction proceeds in ethanol at room temperature via irradiation with green light and with Rose Bengal as the photocatalyst. The product precipitates throug...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 26; no. 8; pp. 4653 - 4658
Main Authors Abramov, Vladimir A, Topchiy, Maxim A, Rasskazova, Maria A, Drokin, Egor A, Tarasova, Ekaterina S, Shurupova, Olga V, Malysheva, Anna S, Rzhevskiy, Sergey A, Beletskaya, Irina P, Asachenko, Andrey F
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 22.04.2024
Subjects
Alkynes
Ethanol
Irradiation
Photocatalysis
Photocatalysts
Precipitates
Room temperature
Sulfones
Water purification
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Summary:A new "green" method for the synthesis of β-iodovinyl aryl and alkyl sulfones with high yield and selectivity has been developed. The reaction proceeds in ethanol at room temperature via irradiation with green light and with Rose Bengal as the photocatalyst. The product precipitates through addition of water and does not need any purification. The photocatalyst was recovered and reused several times after the removal of the solvent. It showed a slight decrease in activity only after the 4th cycle. Photocatalytic iodosulfonylation in ethanol allows the isolation of β-iodovinyl aryl and alkyl sulfones after dilution of the reaction mixture with water and filtration.
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https://doi.org/10.1039/d3gc04810a
Electronic supplementary information (ESI) available: Detailed experimental procedures and
C, 2D NMR, HRMS and IR characterization data. See DOI
ISSN:1463-9262
1463-9270
DOI:10.1039/d3gc04810a