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Ecofriendly Catalytic Aminoselenation of Alkenes: A Green Alternative for Obtaining Potentially Active Compounds
* 1 , 1 , 2 , 3 , 3 , 1
1  Federal Fluminense University
2  Federal University of Santa Catarina
3  University of Perugia

Abstract:

In this work, a new ecological approach to the selenofunctionalization of alkenes has been described. Using I2 as catalyst, DMSO as oxidant, under microwave irradiation (MW) in a solvent- and metal-free method. The general idea is to combine organoselenium compounds and triazole nuclei to obtain molecules capable of becoming a powerful class due to their potential pharmacological activity. However, most methods that involve the functionalization of alkenes are generally mediated by the use of transition metals or reagents in large stoichiometric quantities. Thus, the development of direct, clean and environmentally appropriate procedures, which are in accordance with the principles of Green Chemistry, for the synthesis of these compounds remains highly desirable. Thus, the present work developed the synthesis of β-amino selenides with only 20 minutes of reaction time, following the conditions previously mentioned. After several tests, the optimized condition observed provided a yield of 89% for the product. To verify the viability of the methodology, a variation of 9 diselenides and 11 alkenes was used, obtaining a total of 20 molecules, with yields ranged from 27 to 89%. All synthesized compounds have been fully characterized. In addition, encouraged by these results, the scope of the reaction was expanded using also diorganoil disulfides and ditellurides, obtaining more 13 different molecules with good to excellent yields. Finally, compared to traditional methods, our methodology is a lightweight, metal-free, simple and practical tool for selenofunctionalization of alkenes and is considered a promising alternative in the development of new drugs with potential biological activities.

Keywords: selenium; aminoselenation; green chemistry
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