α-Functionalization of Ketones via a Nitrogen Directed Oxidative Umpolung
Gabriel M. Kiefl, Tanja Gulder
Abstract
Reversing the polarity in molecules is a versatile tool for expanding the boundaries of structural space. Despite a manifold of different umpolung methods available today, overcoming the inherent reactivity still remains a constant challenge in organic chemistry. The oxidative α-functionalization of ketones by external nucleophiles constitute such an example. Herein, we present a hypervalent F-iodane mediated umpolung of pyridyl ketones triggered by Lewis base/Lewis acid noncovalent interactions. A wide variety of external nucleophiles are introduced with high regioselectivity applying this substrate-directing concept.
Topics & Concepts
UmpolungChemistryHypervalent moleculeNucleophileRegioselectivityLewis acids and basesReactivity (psychology)Combinatorial chemistryNon-covalent interactionsOrganic chemistryMoleculeCatalysisReagentMedicinePathologyAlternative medicineHydrogen bondOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions