Systematic study of nucleophile additions to 1-bromo-4-(trifluorovinyloxy)benzene: A versatile intermediate toward fluorinated ethers of synthetic interest

IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR
Scott T. Iacono , Nathan J. Weeks , Dennis W. Smith Jr.
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引用次数: 0

Abstract

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.

Abstract Image

亲核试剂加在1-溴-4-(三氟乙烯氧基)苯上的系统研究:合成感兴趣的氟化醚的通用中间体
氟化醚结构构型的性质已被广泛认为是改进高性能聚合物、工业农用化学品和重要药物靶标的关键组成部分。这是有机氟方法的无数进步的结果,具有这种独特的亚结构,以克服许多传统的合成挑战。在这项工作中,我们通过在高度亲电的芳基三氟乙烯醚中引入异亲核试剂来扩展氟化醚的制备,从而提供了一类新的双官能芳基/烷基氟化醚,可作为有用的中间体。讨论了各种亲核底物的易反应化学,碱对区域选择性的影响,以及合成的芳烷基氟醚的结构解析趋势。
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来源期刊
Journal of Fluorine Chemistry
Journal of Fluorine Chemistry 化学-无机化学与核化学
CiteScore
3.80
自引率
10.50%
发文量
99
审稿时长
33 days
期刊介绍: The Journal of Fluorine Chemistry contains reviews, original papers and short communications. The journal covers all aspects of pure and applied research on the chemistry as well as on the applications of fluorine, and of compounds or materials where fluorine exercises significant effects. This can include all chemistry research areas (inorganic, organic, organometallic, macromolecular and physical chemistry) but also includes papers on biological/biochemical related aspects of Fluorine chemistry as well as medicinal, agrochemical and pharmacological research. The Journal of Fluorine Chemistry also publishes environmental and industrial papers dealing with aspects of Fluorine chemistry on energy and material sciences. Preparative and physico-chemical investigations as well as theoretical, structural and mechanistic aspects are covered. The Journal, however, does not accept work of purely routine nature. For reviews and special issues on particular topics of fluorine chemistry or from selected symposia, please contact the Regional Editors for further details.
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