Catalytic Alkene Carbofunctionalization and Carbodifunctionalization: Catalyst Identification, Reaction Development, and Mechanistic Insights

催化烯烃碳官能化和碳二官能化：催化剂鉴定、反应发展和机理见解

• 批准号: 1955529
• 负责人: Levi Stanley
• 金额: $ 30万
• 依托单位: Iowa State University
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2020
• 资助国家: 美国
• 起止时间: 2020-08-15 至 2022-07-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1955529&HistoricalAwards=false
• 关键词: Catalytic; Alkene; Carbofunctionalization; Carbodifunctionalization; Catalyst

With this Award, the Chemical Synthesis Program of the NSF Division of Chemistry is supporting the research of Dr. Levi Stanley of Iowa State University to develop new chemical reactions that are useful for the field of organic synthesis. Specifically, in this study, the research team is developing chemical reactions that combine simple and readily available chemical building blocks to form new compounds or the ketone class with greater complexity and desirable characteristics. The chemistry being developed adds to the stable of methodology utilized by organic and medicinal chemists to study biological systems and develop therapeutic agents. In particular, the team seeks to develop chemical catalysts that mediate the targeted chemical transformations with high efficiency; this is central to this research program. The research provides a platform for training undergraduate and graduate students to solve important scientific challenges. The nature of the studies enables students to gain skills in multiple areas of chemistry and prepares students for careers that require the ability to solve increasingly interdisciplinary problems. Additional societal benefits are expected to accrue from the planned educational activities to increase retention in STEM disciplines and from new STEM outreach activities for K-12 students and the public in Iowa.Dr. Levi Stanley and his students are developing new chemical reactions and catalysts for the targeted transformations to generate carbonyl compounds that are important to medicinal, process, and materials chemists. The reactions couple readily accessible alkenes and alkynes, carboxylic acid derivatives, and organometallic nucleophiles to form new carbonyl compounds. The studies are driven by a central hypothesis that chemical intermediates generated by activation of carboxylic acid derivatives with a transition metal catalyst can be harnessed to develop a range of new alkene and alkyne functionalization reactions. The new alkene and alkyne functionalization reactions streamline syntheses of carbonyl compounds and provide access to a variety of valuable molecular architectures via new methods to form carbon-carbon bonds. Further broader impacts of this work include training for students in modern synthetic chemistry and catalysis science, increasing STEM retention by engaging undergraduate students in laboratory research experiences, and significant STEM outreach activities.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.

有了这个奖项，NSF化学部的化学合成计划正在支持爱荷华州州立大学的Levi Stanley博士的研究，以开发对有机合成领域有用的新化学反应。具体来说，在这项研究中，研究小组正在开发化学反应，将简单且易于获得的化学结构单元结合起来，形成具有更大复杂性和理想特性的新化合物或酮类。 正在开发的化学增加了有机和药物化学家用于研究生物系统和开发治疗剂的方法的稳定性。 特别是，该团队寻求开发高效介导目标化学转化的化学催化剂;这是该研究计划的核心。该研究为培养本科生和研究生解决重要科学挑战提供了平台。这些研究的性质使学生能够获得化学多个领域的技能，并为需要解决日益跨学科问题的能力的职业做好准备。额外的社会效益预计将从计划中的教育活动，以增加保留在干学科和新的干外展活动的K-12学生和公众在爱荷华州.博士. Levi斯坦利和他的学生正在开发新的化学反应和催化剂的有针对性的转变，以产生羰基化合物，这是重要的医药，工艺和材料化学家.该反应偶联容易获得的烯烃和炔、羧酸衍生物和有机金属亲核试剂以形成新的羰基化合物。这些研究是由一个中心假设驱动的，即通过用过渡金属催化剂活化羧酸衍生物产生的化学中间体可以用来开发一系列新的烯烃和炔烃官能化反应。新的烯烃和炔官能化反应简化了羰基化合物的合成，并通过形成碳-碳键的新方法提供了多种有价值的分子结构。这项工作的更广泛的影响包括对学生进行现代合成化学和催化科学的培训，通过让本科生参与实验室研究经验来提高STEM保留率，以及重要的STEM推广活动。该奖项反映了NSF的法定使命，并通过使用基金会的智力价值和更广泛的影响审查标准进行评估，被认为值得支持。

项目成果

Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes

镍催化乙烯基芳烃的对映选择性硼氢化

• DOI: 10.1021/acs.orglett.1c04073
• 发表时间: 2022
• 期刊: Organic Letters
• 影响因子: 5.2
• 作者: Tran, Hai N.;Stanley, Levi M.
• 通讯作者: Stanley, Levi M.

Palladium-Catalyzed Intermolecular Acylative Heck Reactions with Imides as Acyl Electrophiles

钯催化酰亚胺作为酰基亲电子试剂的分子间酰化 Heck 反应

• DOI: 10.1021/acs.joc.1c00087
• 发表时间: 2021
• 期刊: The Journal of Organic Chemistry
• 作者: Kadam, Abhishek A.;Metz, Tanner L.;David, Colton M.;Koeritz, Mason T.;Stanley, Levi M.
• 通讯作者: Stanley, Levi M.