Impact of Multiple Hydrogen Bonds with Fluoride on Catalysis: Insight from NMR Spectroscopy
Francesco Ibba, Gabriele Pupo, Amber L. Thompson, John M. Brown, Timothy D. W. Claridge, Véronique Gouverneur
Abstract
-butylammonium fluoride (TBAF) or CsF. Structure-activity analysis reveals that the three hydrogen-bond contacts with fluoride are not equal in terms of their contribution to catalyst efficacy, suggesting that tuning individual electronic environment is a viable approach to control phase-transfer ability and enantioselectivity.
Topics & Concepts
ChemistryFluorideNucleophileCatalysisHydrogen bondHydrogen fluorideEnantioselective synthesisNuclear magnetic resonance spectroscopyInorganic chemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryMoleculeFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsMetal-Organic Frameworks: Synthesis and Applications