Novel Polyfluoroalkylated Building Blocks

通过这一奖项，化学系化学合成项目支持宾夕法尼亚大学加里·莫兰德教授在开发一类氟化有机化合物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）稳定性有深远影响。通过开发各种碳-碳和碳-杂原子协议，正在构建多用途、稳定、全氟烷基取代的构建块家族，这些构建块可以大量安装。这些制度的成功将为合成具有广泛氟化的有机分子提供方法，通过在高度趋同但模块化的合成过程中增加分子复杂性的方法，扩大和创造新的化学空间。因此，这些高度灵活的预制亚基为构建分子库提供了一个平台，可以在制药或农化工业的背景下研究其性质，例如，促进具有独特性质的新化合物的发现，并为这些行业提供新的工具，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特性的重要性已得到牢固确立，因此，选择性地引入三氟甲基以及多氟烷基已引起合成界的高度兴趣。这些努力大多支持在芳香体系上安装氟或三氟甲基。相比之下，将功能化的全氟亚基纳入烷基体系的一般方法，特别是以对映选择性的方式，发展得还不完善，但在结构多样性和扩大化学空间方面却日益重要。将进行的研究将允许开发操作简单和有效的途径来硼化有机氟材料。研究的第一个子目标是开发一种方便的多种稳定的多氟烷基硼试剂的合成方法，用于将全氟烷基单位纳入烷基亚结构。

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.