Trichloroisocyanuric Acid (TCCA): A Suitable Reagent for the Synthesis of Selanyl‐benzo[b]chalcogenophenes

Abstract

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.

Synthesis of 3-selanyl-isoflavones from 2-hydroxyphenyl enaminones using trichloroisocyanuric acid (TCCA): a sustainable approach

“…Based on the literature 13 and the data collected from a set of control experiments that are described in the supplementary material, we suggest a plausible mechanism as depicted in Scheme 4. We assume that the reaction between diselenide 2 and TCCA occurs previous to any interaction with enaminone 1 , in order to generate electrophilic selenium species I and/or II , or maybe both.…”

“…Recently, some research groups have demonstrated the generation of electrophilic selenium species from diorganoyl diselenides, through the use of the cheap and non-toxic chlorinating agent trichloroisocyanuric acid (TCCA), under mild conditions. 13…”

Antidepressant Potential of a Functionalized 3-Selanyl Benzo[b]Furan Compound in Mice: Focus on the Serotonergic System

“…The compounds 3-selanyl benzo[ b ]furans (SeBZF 1–5 ) (Figure ), named 2-phenyl-3-(phenylselanyl)benzofuran (SeBZF 1 ), 3-((4-fluorophenyl)selanyl)-2-phenylbenzofuran (SeBZF 2 ), 3-((4-methoxyphenyl) selanyl)-2-phenylbenzofuran (SeBZF 3 ), 3-((4-chlorophenyl)selanyl)-2-phenylbenzofuran (SeBZF 4 ), and 2-phenyl-3-(4-tolylselanyl)benzofuran (SeBZF 5 ), were synthesized and characterized in the Laboratory of Synthesis of Selenium and Tellurium Derivatives (LabSelen) located at the Federal University of Santa Catarina (UFSC) employing the method previously described by Blödorn et al 1-Methoxy-2-(phenylethynyl)benzene (1.0 mmol), corresponding diaryl diselenide (0.55 mmol), EtOH (1.5 mL), and TCCA (0.33 equiv = 0.060 g) were added to a 10.0 mL reaction balloon. Then, the reaction mixture was allowed to react at room temperature for 1 h. After completion of the reaction, the mixture was extracted with ethyl acetate and washed with water, dried over MgSO 4 , and concentrated under vacuum.…”

Synthesis of 3‐Arylselanyl Benzothiophenes through Visible‐Light‐Mediated Radical Cyclization

“…The data that support the findings of this study are available in the supplementary materials of this article. Additional references cited within the Supporting Information [24–26] …”

“…In 2019, Perin and Lenardão reported a synthesis of 2,3‐bis‐selenylated benzothiophenes using electrophilic selenium species generated in situ by the reaction of Oxone and diselenides under the reflux conditions in ethanol (Scheme 1, A1) [10,11] . Recently, Neto and Alves developed a synthesis for 3‐selanyl benzothiophenes promoted by trichloroisocyanuric acid (TCCA) [12] . The reactions were performed with in situ generated electrophilic selenium species formed from diselenides and TCCA.…”