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

Iowa State University, Ames IA

Investigators

Abstract

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.