Discoveries in chemical catalysis enable the efficient synthesis of new small molecules and materials with broad impact on pharmaceutical research, material science, and biomedical research. Catalysis using Lewis bases, and in particular, N-heterocyclic carbenes (NHCs) has exploded during the last decade and this area is poised for great advances over the next two decades. These unique Lewis bases have been employed as ligands to generate chiral metal complexes as well as catalysts in their own right without transition metals (metal free or organocatalysis). However, there is a current dearth of new chiral Lewis bases for chemical reactions of high value and a limited number of mechanistic investigations of NHC-catalyzed processes. The lack of deep understanding and new classes of NHCs currently limits the potential applications of NHC-metal complexes and carbene catalysis. Our integrated synthetic and mechanistic studies build on our successful past activities and will create multiple new classes of azolium salts to be deployed as potential catalysts and novel ligands. This plan will continue to explore planar chiral NHCs as well as develop additional new families of chiral NHCs as ligands and catalysts. The key synergy in these studies is the integration of mechanistic information, characterization data and test bed experiments to create new NHC species with an understanding of their potential and fundamental reactivity. The new NHCs generated during the proposal period will be evaluated as ligands in high value stereoselective transformations as well as organocatalysts. We will rely on our extensive knowledge and experience in the areas of methodology and catalysis to guide our investigations and to integrate discoveries into new synthetic processes. The goals of this work are to: • Investigate new, catalytic -borylation reactions with planar chiral NHC-Cu(I) complexes • Create new classes of chiral N-heterocyclic carbenes • Evaluate these NHCs in catalytic processes (both metal and organocatalysis) • Investigate new modular strategies for expedited chiral NHC construction • Understand the structure reactivity relationships of new catalysts for the purpose of predicting and controlling the outcome of future Lewis base processes
|Effective start/end date||8/1/17 → 7/31/22|
- National Science Foundation (CHE-1665141)
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