Departamento de Química Orgánica, Universitat de València, 46100 Burjassot, Spain.
Departamento de Química Orgánica e Inorgánica, Avda. Julián Clavería nº 8, 33006 Oviedo, Spain.
Molecules. 2019 Apr 20;24(8):1569. doi: 10.3390/molecules24081569.
Organofluorine compounds are finding increasing application in a variety of fields such as pharmaceutical, agrochemical, and material sciences. However, given the scarcity of fluorine-containing natural products, advancement in this area depends almost entirely on the development of new synthetic methodologies. In this article, we present the synthesis of a series of previously undescribed ()-β-fluorovinyl sulfones via a simple copper-catalyzed addition of hydrogen fluoride to alkynyl sulfone starting materials in varying yields and selectivities. The hydrogenation of these products was also explored and compared with the hydrogenation of the related isomers. These new products may find interesting applications, given the versatility of vinyl sulfones in chemical synthesis and the unique properties of vinyl fluorides in biological settings.
有机氟化合物在药物、农化和材料科学等多个领域的应用日益广泛。然而，鉴于含氟天然产物的稀缺性，该领域的进展几乎完全依赖于新合成方法的开发。在本文中，我们通过简单的铜催化氟化氢加成到炔基砜起始原料的方法，以不同的产率和选择性合成了一系列以前未描述的 ()-β-氟乙烯基砜。还探索了这些产物的加氢反应，并与相关异构体的加氢反应进行了比较。鉴于乙烯基砜在化学合成中的多功能性以及乙烯基氟化物在生物环境中的独特性质，这些新产品可能具有有趣的应用前景。
