Novel Polyfluoroalkylated Building Blocks

新型多氟烷基化结构单元

• 批准号: 1362841
• 负责人: Gary Molander
• 金额: $ 45万
• 依托单位: University of Pennsylvania
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2014
• 资助国家: 美国
• 起止时间: 2014-07-01 至 2018-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1362841&HistoricalAwards=false
• 关键词: Novel; Polyfluoroalkylated; Building; Blocks

Through this award, the Chemical Synthesis Program of the Division of Chemistry supports work by Professor Gary Molander of the University of Pennsylvania in developing synthetic approaches to a class of fluorinated organic compounds. The presence of fluorine in organic molecules is known to have profound effects upon bioavailability and/or stability. Families of versatile, stable, perfluoroalkyl-substituted building blocks are being constructed that can be installed in large fragments through the development of a variety of carbon-carbon and carbon-heteroatom protocols. Success in these regimes will provide methods for the synthesis of organic molecules with extensive fluorination, expanding and creating novel chemical space by methods that increase molecular complexity in highly convergent yet modular synthetic processes. These highly flexible, prefabricated subunits thus provide a platform around which to build libraries of molecules for investigation of their properties within the context of the pharmaceutical or agrochemical industries, for example, facilitating the discovery of novel compounds with unique properties and providing these industries new tools to bring innovative molecules to the market more efficiently and at lower cost. The importance of embedding fluorine atoms within organic molecules to alter their physicochemical and biological properties has been firmly established, and thus the selective introduction of trifluoromethyl groups, as well as polyfluorinated alkyl groups, has consequently been of high interest to the synthesis community. Most of these efforts have supported the installation of fluoro- or trifluoromethyl groups onto aromatic systems. By contrast, general methods for the incorporation of functionalized, perfluorinated subunits into alkyl systems, particularly in an enantioselective manner, is much less well developed, yet increasingly more important in terms of structural diversity and expanding chemical space. The research to be carried out will allow the development of operationally simple and effective routes to borylated organofluorine materials. The first subgoal of the investigations is to develop convenient syntheses of a diverse family of stable, polyfluorinated alkylboron reagents to be used for the incorporation of perfluoroalkyl units into alkyl substructures.

通过这个奖项，化学系的化学合成计划支持宾夕法尼亚大学的加里莫兰德教授在开发一类含氟有机化合物的合成方法方面的工作。 已知有机分子中氟的存在对生物利用度和/或稳定性具有深远的影响。 正在构建通用的、稳定的、全氟烷基取代的结构单元的家族，其可以通过开发各种碳-碳和碳-杂原子方案以大片段安装。 在这些制度的成功将提供的方法，用于有机分子的合成与广泛的扩展，扩大和创造新的化学空间的方法，增加分子的复杂性，在高度收敛，但模块化的合成过程。 因此，这些高度灵活的预制亚单元提供了一个平台，围绕该平台构建分子库，用于在制药或农业化学工业的背景下研究其性质，例如，促进发现具有独特性质的新型化合物，并为这些工业提供新的工具，以更有效和更低的成本将创新分子推向市场。 在有机分子中嵌入氟原子以改变其物理化学和生物学性质的重要性已经被牢固地确立，因此选择性引入三氟甲基以及多氟化烷基因此引起了合成界的高度兴趣。这些努力中的大多数支持将氟或三氟甲基基团安装到芳族体系上。相比之下，将官能化的全氟化亚基引入烷基体系中的一般方法，特别是以对映选择性方式，发展得不那么好，但在结构多样性和扩大化学空间方面越来越重要。 即将开展的研究将有助于开发操作简单和有效的硼化有机氟材料路线。 调查的第一个子目标是开发一个稳定的，多氟化烷基硼试剂的不同家庭的方便的合成，用于将全氟烷基单元纳入烷基亚结构。