Trichloroisocyanuric Acid (TCCA): A Suitable Reagent for the Synthesis of Selanyl‐benzochalcogenophenes

A new approach for the synthesis of 3‐organoselanyl‐benzo[b]chalcogenophenes promoted by trichloroisocyanuric acid is reported. The reaction was carried out with electrophilic selenium species which were generated in situ by the reaction between trichloroisocyanuric acid and diorganyl diselenides us...

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Published inEuropean journal of organic chemistry Vol. 2022; no. 40
Main Authors Blödorn, Gustavo B, Duarte, Luis Fernando B, Roehrs, Juliano A, Silva, Márcio S, Neto, José S S, Alves, Diego
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.10.2022
Subjects
Chemical synthesis
Ethanol
NMR spectroscopy
Reaction mechanisms
Reagents
Selenides
Selenium
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Summary:A new approach for the synthesis of 3‐organoselanyl‐benzo[b]chalcogenophenes promoted by trichloroisocyanuric acid is reported. The reaction was carried out with electrophilic selenium species which were generated in situ by the reaction between trichloroisocyanuric acid and diorganyl diselenides using ethanol as solvent. The developed method uses mild reaction conditions and was efficient for the synthesis of different 3‐organoselanyl‐benzo[b]chalcogenophenes in a good to excellent yields. Analysis of 77Se NMR spectroscopy indicates that the electrophilic PhSeCl was formed in situ and a plausible reaction mechanism was proposed.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200775