The Synthetic Use of Lewis and Bronsted Acid Catalyzed Electrophilic Deborylations

在化学系化学合成项目的支持下，休斯顿大学的Jeremy A. May教授正在开发新的方法，将碳硼键的试剂偶联到其他有机片段上，从而在控制立体化学的情况下快速获得复杂的分子支架。这些反应继续与有机硼烷试剂形成新的碳-碳键，并解决了需要重金属的相关合成方法的局限性。这项工作旨在建立控制三维分子结构中C-C键形成的新方法。该方法旨在改善具有医学相关生物活性的分子的化学合成。梅教授还与休斯敦的一所文科学校KIPP Sharpstown初中合作，向学生介绍实验化学和其他物理科学。这种伙伴关系为弱势和有风险的学生提供了机会，增强他们对科学的理解，并为上大学做准备。May教授和他的研究团队正在开发新的方法来激活和控制有机硼烷的亲核添加物，目标是在结构复杂的有机框架内构建具有挑战性的碳-碳键。Lewis和Bronsted酸催化剂在立体化学控制下将这些添加物促进成各种亲电有机片段的能力将被研究。要研究的转化包括涉及杂环有机硼烷和其他功能的例子，这些功能通常与过渡金属催化的碳-碳键形成策略不相容。亲电酰化方法在环化反应和天然产物合成中得到了进一步的测试。这些活动预计将协同为合成化学的研究生和本科生提供优秀的培训。该奖项反映了美国国家科学基金会的法定使命，并通过使用基金会的知识价值和更广泛的影响审查标准进行评估，被认为值得支持。

With the support of the Chemical Synthesis Program in the Division of Chemistry, Professor Jeremy A. May of the University of Houston is developing new ways to couple reagents with carbon-boron bonds to other organic fragments to rapidly access complex molecular scaffolds with control of stereochemistry. These reactions proceed to form new carbon-carbon bonds with organoborane reagents and address limitations of related synthetic methodologies that require heavy metals. This work is directed at establishing new methods to control C-C bond formation in three-dimensional molecular structures. The methodology is targeted toward improving the chemical synthesis of molecules with medicinally relevant biological activity. Professor May is also collaborating with KIPP Sharpstown Junior High, a liberal arts-focused school in Houston, to introduce the students to experimental chemistry and other physical sciences. This partnership provides disadvantaged and at-risk students the opportunity to bolster their scientific understanding and desire to prepare for college. Professor May and his research team are developing new ways to activate and control nucleophilic additions of organoboranes with the goal of constructing challenging carbon-carbon bonds within architecturally complex organic frameworks. Lewis and Bronsted acid catalysts will be investigated for their ability to promote these additions into a variety of electrophilic organic fragments with stereochemical control. The transformations to be studied include examples involving heterocyclic organoboranes and other functionalities that are often incompatible with transition metal-catalyzed carbon-carbon bond forming strategies. Electrophilic deborylation approaches are further being tested in annulation reactions and natural product synthesis. These activities are expected to synergistically provide excellent training for a diverse group of graduate and undergraduate students in synthetic 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.