Ecofriendly Catalytic Aminoselenation of Alkenes: A Green Alternative for Obtaining Potentially Active Compounds

L. Gomes, Rafaella G. Angelino, José Neto, I. D. Leo, C. Santi, Vanessa Nascimento
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Abstract

: In this work, a new ecological approach to the selenofunctionalization of alkenes has been described using I 2 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. In addition, encouraged by these results, the scope of the reaction was expanded using also diorganoil disulfides and ditellurides, obtaining molecules with good to excellent yields. Finally, compared to traditional methods, our methodology is a lightweight, metal-free, simple and practical tool for the selenofunctionalization of alkenes and is considered a promising alternative in the development of new drugs with potential biological activities.
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烯烃的生态催化氨基硒化:一种获得潜在活性化合物的绿色替代方法
在这项工作中,描述了一种新的生态方法,在微波辐射(MW)下,以i2为催化剂,DMSO为氧化剂,在无溶剂和金属的方法下进行烯烃的硒功能化。一般的想法是结合有机硒化合物和三唑核,以获得由于其潜在的药理活性而能够成为强大类的分子。然而,大多数涉及烯烃功能化的方法通常是通过使用过渡金属或大量化学计量量的试剂来介导的。因此,开发符合绿色化学原则的直接、清洁和环境适宜的程序来合成这些化合物仍然是非常需要的。因此,在上述条件下,本工作仅用20分钟的反应时间合成了β -氨基硒化物。此外,受这些结果的鼓舞,扩大了反应的范围,也使用了二有机油二硫化物和二碲化物,得到了收率从良好到优异的分子。最后,与传统方法相比,我们的方法是一种重量轻、无金属、简单实用的烯类硒功能化工具,被认为是开发具有潜在生物活性的新药的一种有前景的替代方法。
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