01/30/20 - 9:45 AM to 11:00 AM
Department Seminar: Professor Levi Stanley
Catalytic Alkene Hydroacylation and Carboacylation Reactions and Serendipitous Discoveries Along the Way
Carbon-carbon bond-forming processes to generate ketones and related carbonyl compounds are among the most important reactions to medicinal, process, and materials chemists who prepare molecules to study biological systems, treat human disease, and create functional materials. Over the past decade, my group has established programs aimed at developing reactions and catalysts that enable rapid synthesis of heterocyclic and carbocyclic ketones through transition metal-catalyzed alkene and alkyne hydroacylation reactions and formal hydroarylations and hydroheteroarylations of activated alkenes. More recently, we reported a new approach to alkene carboacylation based on Ni-catalyzed amide C-N bond activation that sets the stage for the new alkene functionalization reactions included in this presentation. This foundation of reaction development in the area of transition metal-catalyzed alkene functionalization has led to discovery of new catalytic, intermolecular carbacylation reactions of alkenes and alkynes to generate densely functionalized ketones, the development of complementary catalysts for acylative Mizoroki-Heck reactions of alkenes, and the serendipitous discovery of an enantioselective nickel catalyst for formal hydroarylation of activated alkenes.
Professor Levi Stanley earned his bachelor's in chemistry from Augustana College in South Dakota and his doctorate at North Dakota State University, where he developed enantioselective dipolar cycloadditions and studied applications of chiral relay ligands and auxiliaries in enantioselective catalysis. After receiving his doctorate, he moved to the University of Illinois at Urbana-Champaign as a post-doctoral fellow, studying iridium-catalyzed allylic substitution reactions and the application of C-H functionalization and a-arylation reactions to natural product synthesis. He also received a Pathways to Independence Award from the National Institutes of Health to develop a new platform for the generation of artificial metalloenzyme catalysts. He joined the faculty at Iowa State University in January 2012.
Research in Professor Stanley's Laboratory focuses on the identification of catalysts and the development of synthetic methods that streamline the synthesis of medicinally and industrially important molecules. Areas of interest include: 1) the development of new metal-catalyzed alkene functionalization reactions; 2) the development of new synthetic methods to form and functionalize heterocycles; and 3) the identification and development of catalysts that lie at the interface of traditional homogeneous and heterogeneous catalysis. Students in the Stanley group learn synthetic organic chemistry, heterocyclic chemistry, catalytic reaction development, asymmetric synthesis and catalysis, and materials synthesis and characterization. These skills are leveraged to address challenges in the development of new alkene hydroacylation and carboacylation reactions, the synthesis of quaternary carbon stereocenters, the synthesis of metal-organic frameworks (MOFs) and covalent organic frameworks (COFs), and the application of MOFs and COFs as catalysts of valuable organic reactions.