Organocalcogenides, in particular, organoselenium compounds have been widely studied due to the large number of synthetic and biological applications. Among organoselenium compounds, a class of bis-selenide-alkene derivatives has attracted attention. Recently, some studies have been developed to the synthesis of vinyl chalcogen derivatives, since these are also highly valuable intermediates in several synthetic applications. However, the methodologies developed so far have extensive reaction times, use of toxic solvents and heavy metals. Therefore, there is an emerging need to develop protocols for the synthesis of these molecules that are in accordance with the principles of green chemistry. In this work, we developed an alternative synthesis of bis-selenium-alkene derivatives, through an environmentally appropriate methodology. Reaction optimization was evaluated from the diphenylacetylene and diphenyl diselenide, using I2/DMSO as a catalytic system under microwave irradiation or conventional heating. The variations of these conditions were carried out through different equivalences between the reagents, the amount of catalyst (I2), temperature, DMSO and the reaction process (MW or conventional). Even now, it was found that the best established condition was using diphenylacetylene, diphenyl diselenide, 30mol% I2 in DMSO, under conventional heating at 100°C for 10min. In this condition the product was obtained in 82% yield and its characterization was performed using 1H and 13C NMR spectroscopy. Therefore, the methodology that is being developed, in addition to perfectly attending to the principles of green chemistry, will allow to evaluate the reaction scope using different alkenes and diselenides or even disulfides and ditellurides.
Efficient Eco-Friendly Solvent-Free Obtaining Bis-Selenium-Alkenes with High Biological Potential
Published: 09 November 2020 by MDPI in 1st International Electronic Conference on Catalysis Sciences session Invited Session. e-WSeS 2020
Keywords: catalysis; grenn chemistry; environment; synthesis