Organic Chemistry Seminar

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.