Organic synthesis and materials chemistry via catalytic organoborane chemistry

通过催化有机硼烷化学进行有机合成和材料化学

• 批准号: 194284-2010
• 负责人: Crudden, Catherine
• 金额: $ 6.56万
• 依托单位: Queen's University
• 依托单位国家: 加拿大
• 项目类别: Discovery Grants Program - Individual
• 财政年份: 2013
• 资助国家: 加拿大
• 起止时间: 2013-01-01 至 2014-12-31
• 项目状态: 已结题
• 来源: https://www.nserc-crsng.gc.ca/ase-oro/Details-Detailles_eng.asp?id=523162
• 关键词: Organic; synthesis; materials; chemistry; via

The ability to prepare complex organic molecules efficiently has been critical in the development of the pharmaceutical industry. Recently, similar abilities have become important in areas such as liquid crystals and organic electronics. In this case, the molecules employed must be free of isomers and other contaminants that may impact performance. Thus, state-of-the-art synthetic techniques to prepare molecules for materials applications is critical. In the case of pharmaceutical applications of organic molecules, the most urgent need is for new structures that have not been made previously and may have unique physiological activities. For these reasons, we propose to examine the synthesis of two novel classes of molecules with applications in the pharmaceutical and materials areas. Chiral 1,1-diaryl alkanes are molecules that are exceedingly difficult to make by existing routes, yet these provide novel chiral scaffolds that are of interest to the pharmaceutical industry and materials chemistry. Likewise, the chiral 1,1,1-triarylmethanes and alkanes are virtually unknown in their enantiomerically pure state. We have proposed routes to prepare these important classes of compounds based on recent chemistry from our lab. The routes provide compounds of >95% optical and isomeric purity. In our second area of research, we propose to employ frustrated Lewis pair (FLP) chemistry for the activation of alkane C-H bonds. When an acidic and a basic molecule are present in solution but are inhibited (usually by sterics) from reacting with each other they are said to be a Frustrated Lewis Pair. In this case, the molecules can cooperate to split relatively unreactive bonds such as H-H, H-Si and H-B. We plan to employ this method for the activation of C-H bonds, which is a critical goal in terms of synthesis and energy since effective C-H activation strategies could better utilize petroleum feedstocks. Initially we will use organic structures that are biased towards the desired reaction in order to demonstrate feasibility, but we plan to move toward organic molecules with less and less functionality. HQP involved in this chemistry will gain a wide range of expertise in the area of organic synthesis, catalysis, air sensitive techniques and materials chemistry.

高效制备复杂有机分子的能力在制药工业的发展中至关重要。最近，类似的能力在液晶和有机电子等领域变得重要。 在这种情况下，所采用的分子必须不含可能影响性能的异构体和其他污染物。 因此，制备用于材料应用的分子的最先进的合成技术是至关重要的。 在有机分子的药物应用的情况下，最迫切的需要是以前没有制造的新结构，并且可能具有独特的生理活性。 由于这些原因，我们建议研究两类新型分子的合成，并在药物和材料领域中应用。 手性1，1-二芳基烷烃是极难通过现有途径制备的分子，但这些提供了对制药工业和材料化学感兴趣的新型手性支架。 同样，手性1，1，1-三芳基甲烷和烷烃在其对映体纯状态下几乎是未知的。 我们已经提出了路线，以制备这些重要类别的化合物的基础上，从我们的实验室最近的化学。 这些路线提供了光学纯度和异构体纯度>95%的化合物。 在我们的第二个研究领域，我们建议采用阻挫刘易斯对（FLP）化学的烷烃C-H键的活化。 当一个酸性分子和一个碱性分子存在于溶液中，但被抑制（通常被空间位阻物质抑制）彼此反应时，它们被称为受抑刘易斯对。 在这种情况下，分子可以合作分裂相对不反应的键，如H-H，H-Si和H-B。我们计划采用这种方法来活化C-H键，这在合成和能量方面是一个关键目标，因为有效的C-H活化策略可以更好地利用石油原料。 最初，我们将使用偏向于所需反应的有机结构，以证明可行性，但我们计划向功能越来越少的有机分子发展。 参与该化学的HQP将获得有机合成，催化，空气敏感技术和材料化学领域的广泛专业知识。