RUI: New Synthetic Methods for CB11 Carboranes

化学部化学合成计划支持Marcus Juhasz教授的项目。Juhasz教授是惠特曼学院化学系的教员。他研究的是由稳定的硼原子核心团簇构成的分子。这些分子具有独特的性质，长期以来一直令人感兴趣的是开发用于医疗应用的新治疗和成像试剂，用于工业重要化学反应的新催化剂，以及新的先进光学和电子材料。然而，尽管人们对此感兴趣，但这些分子的用途有限。这在很大程度上是因为缺乏能够制备它们的合成方法。Juhasz教授和他的团队正在进行的研究的目标就是解决这个问题。因此，他们正在努力开发有效的方法来制备新的硼团簇。除了这些科学目标之外，正在开发的反应还为在有机化学和无机化学的子领域教育理科学生提供了极好的机会。化学有可能产生很大的影响，而且推动这一努力的本科生也可以接触到它。作为一家小型本科院校的教师兼学者，Juhasz教授很有能力培训和密切指导那些在科学领域代表性不足的学生。阴离子硼簇合物CHB11H11-(CB11)是一种非常稳定的分子，其衍生物在催化、医药和先进材料等领域具有广泛的应用前景。生产CB11衍生物的合成方法在很大程度上仍未被探索。这项建议的首要目标是开发新的合成方法，通过追求三个具体的合成目标来制备有用的CB11衍生物。目标1是在硼的顶点引入酯和酰胺官能团，通过两步合成与羧酸中间体将酰胺和酯连接到CB11笼子中的硼原子上。目标2正在扩展现有的氰化策略(通过优化催化剂、溶剂和微波辐射参数)来制备高度氰化的CB11簇合物。AIM 3正在开发一种通过改进的Suzuki偶联反应引入烷基和芳基取代基的通用方法。该提议正在制备CB11碳硼烷簇合物的潜在有用的衍生物。此外，该项目通过让本科生沉浸在合成有机和无机化学的尖端研究中，为未来的科学家提供高水平的培训和教育。该奖项反映了NSF的法定使命，并通过使用基金会的智力优势和更广泛的影响审查标准进行评估，被认为值得支持。

The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Marcus Juhasz. Professor Juhasz is a faculty member in the Department of Chemistry at Whitman College. He investigates molecules constructed from a stable core cluster of boron atoms. These molecules have unique properties that have long been of interest for the development of new therapeutic and imaging agents for medicinal applications, new catalysts for industrially-important chemical reactions, and new advanced optical and electronic materials. Yet in spite of this interest, the molecules have seen limited use. This is in large part because of a lack of synthetic methods that allow for their preparation. The goal of the research being pursued by Professor Juhasz and his group is to solve this problem. Accordingly, they are working to develop efficient approaches for the preparation of new boron clusters. In addition to these scientific goals, the reactions being developed provide excellent opportunities to educate science students in the subfields of organic and inorganic chemistry. The chemistry has the potential for high impact, and it is accessible to the undergraduates who are driving the effort. As a teacher-scholar at a small undergraduate institution, Professor Juhasz is well positioned to train and closely mentor students who are underrepresented in science. The anionic boron cluster CHB11H11- (CB11) is a very stable molecule whose derivatives are attractive for a variety of applications, including catalysis, medicine, and advanced materials. Synthetic methods for producing derivatives of CB11 have remained largely unexplored. The overarching goal of this proposal is to develop new synthetic methods for preparing useful derivatives of CB11, by pursuing three specific synthetic aims. Aim 1 is introducing ester and amide functional groups at boron vertices employing a two-step synthesis with a carboxylic acid intermediate to attach amides and esters to boron atoms in the CB11 cage. Aim 2 is expanding an existing cyanation strategy (through optimization of the catalyst, solvent, and microwave-irradiation parameters) to prepare highly cyanated CB11 clusters. Aim 3 is developing a versatile method for introducing alkyl and aryl substituents via an adapted Suzuki coupling reaction. The proposed is preparing potentially useful derivatives of CB11 carborane clusters. Moreover, this project is providing a high level of training and education for future scientists by immersing undergraduate students in cutting-edge research in synthetic organic and inorganic chemistry.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.