Organic Chemistry Seminar
Huw M. L. Davies is the Asa Griggs Candler Professor of Organic Chemistry at Emory University. His research focuses on the development of new enantioselective synthetic methods. His program covers design of chiral catalysts, metal carbene chemistry, development of new synthetic methodology, total synthesis of biologically active natural products, and development of chiral therapeutic agents. A major current theme of his program is catalytic asymmetric C–H functionalization by means of rhodium-carbene induced C–H insertion. He is actively involved in developing communities for collaborative and synergistic research. He was the Director of the NSF Phase II Center for Chemical Innovation for Selective C-H Functionalization between 2009-2022 and is now the Director of the Catalysis Innovation Consortium, consisting of 46 professors from 28 universities. His awards including the American Chemical Society Cope Scholar Award (2005), the Encyclopedia of Reagents for Organic Synthesis Reagent of the Year Award (2013), Paul Rylander Award (from the Organic Reactions and Catalysis in Synthesis Society) (2018), and the ACS HC Brown Award for Creative Research in Synthetic Methods (2019). He is an elected Fellow of the Royal Society of Chemistry, the American Chemical Society, and the American Association for the Advancement of Science.
A major challenge in organic synthesis is the selective functionalization of C–H bonds. As most organic compounds contain multiple C–H bonds with similar properties, distinguishing between them requires precise control. In this study, we show how transition metal catalysts can adopt many of the characteristics associated with enzymes, leading to unprecedented site-selectivity in the C–H functionalization step. The catalysts are dirhodium complexes that adopt a bowl-shape on formation. The flexible microenvironment within the bowl causes an induced fitting to occur when the reagent and the substrate approach the catalyst. The key factors controlling the selectivity are noncovalent interactions between the approaching substrate and the catalyst wall, placing a specific C–H bond in the substrate close to the metal-bound reagent. This presentation will describe the development of new types of dirhodium catalysts and illustrate the range of selective C-H functionalization that can be achieved with these catalysts.