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Systematic study of nucleophile additions to 1-bromo-4-(trifluorovinyloxy)benzene: A versatile intermediate toward fluorinated ethers of synthetic interest
Journal of Fluorine Chemistry ( IF 1.9 ) Pub Date : 2023-09-16 , DOI: 10.1016/j.jfluchem.2023.110187
Scott T. Iacono , Nathan J. Weeks , Dennis W. Smith

The nature of the structural configuration of fluorinated ethers has been widespread as a crucial component for improving high performance polymers, industrial agrochemicals, and targets for important pharmaceutical drugs. This is a result of countless advances in organo-fluorine methodologies with this unique substructure in order to overcome many traditional synthetic challenges. In this work, we expand on the preparation of fluorinated ethers by introducing hetero-nucleophiles to a highly electrophilic aryl trifluorovinyl ether affording a new class of difunctional aryl/alkyl fluorinated ethers that would serve as useful intermediates. The facile reaction chemistry of various nucleophile substrates, effect of base concerning regio-selectivity, and structural elucidation trends of the synthesized aryl/alkyl fluoroethers will be discussed.



中文翻译:

1-溴-4-(三氟乙烯氧基)苯亲核试剂加成的系统研究:合成氟化醚的多功能中间体

氟化醚的结构构型性质已广泛作为改善高性能聚合物、工业农用化学品和重要药物靶标的关键成分。这是有机氟方法学无数进步的结果,具有这种独特的子结构,以克服许多传统的合成挑战。在这项工作中,我们通过将杂亲核试剂引入高度亲电子的芳基三氟乙烯基醚来扩展氟化醚的制备,提供一类新的双官能芳基/烷基氟化醚,可用作有用的中间体。将讨论各种亲核底物的简单反应化学、碱对区域选择性的影响以及合成的芳基/烷基氟代醚的结构阐明趋势。

更新日期:2023-09-16
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