Anghinoni João M, Ferreira Sabrina S, Piquini Paulo C, Iglesias Bernardo A, Perin Gelson, Penteado Filipe, Lenardão Eder J
Centro de Ciências Químicas, Farmacêuticas e de Alimentos - CCQFA, Universidade Federal de Pelotas - UFPel, P. O. box 354, 96010-900, Pelotas, RS, Brazil.
Departamento de Física, Universidade Federal de Santa Maria, Av. Roraima, Building 13, 97105-900, Santa Maria, RS, Brazil.
Chemistry. 2023 Oct 23;29(59):e202301934. doi: 10.1002/chem.202301934. Epub 2023 Sep 22.
Herein, we describe a new method for the synthesis of α-carbonyl selenocyanates by reacting triselenium dicyanide (TSD) and styrenes under blue light irradiation and O atmosphere. The reactions are triggered by the formation of Se-centered radical species, followed by the addition/oxidation of the styrene π-bond. α-Carbonyl selenocyanates and α-hydroxy selenocyanates were obtained in moderate to excellent yields from aryl- and alkyl-substituted alkenes, respectively. It was demonstrated that α-carbonyl selenocyanates could be used as a synthetic platform in a multicomponent reaction strategy to prepare 2-phenylimidazo[1,2-a]pyridine derivatives, which were evaluated for their photophysical properties. Overall, this new method provides a useful tool for synthesizing α-carbonyl selenocyanates, and demonstrates their potential for use in the synthesis of other compounds, thus giving new synthetic opportunities to construct organic selenocyanate compounds.
在此，我们描述了一种在蓝光照射和氧气氛围下，通过三硒二氰化物（TSD）与苯乙烯反应合成α-羰基硒氰酸酯的新方法。反应由以硒为中心的自由基物种的形成引发，随后是苯乙烯π键的加成/氧化反应。分别从芳基和烷基取代的烯烃中以中等至优异的产率获得了α-羰基硒氰酸酯和α-羟基硒氰酸酯。结果表明，α-羰基硒氰酸酯可作为多组分反应策略中的合成平台，用于制备2-苯基咪唑并[1,2-a]吡啶衍生物，并对其光物理性质进行了评估。总体而言，这种新方法为合成α-羰基硒氰酸酯提供了一种有用的工具，并展示了它们在合成其他化合物方面的潜力，从而为构建有机硒氰酸酯化合物提供了新的合成机会。
