Palladium-Catalyzed Arylation of Hydantoins with Aryl Chlorides Enabled by Ylide-Functionalized Phosphines (YPhos)
Florian Papp, Daniel Sowa Prendes, Sourav Manna, Ann‐Katrin Seitz, Sofiya Kostiukovska, Julian Löffler, Viktoria H. Gessner, Lukas J. Gooßen
Abstract
The hydantoin moiety is an important structural motif present in various pharmaceuticals. Palladium complexes bearing electron-rich, bulky ylide-functionalized phosphine (YPhos) ligands were found to catalyze the arylation of N -protected hydantoins with broadly available aryl chlorides. Selective monoarylations, sequential diarylations, and arylation-alkylation sequences have been achieved. In combination with stepwise deprotection strategies, this opens up an expedient access to a wide variety of hydantoins, including derivatives of the anticonvulsant drugs phenytoin and mephenytoin.
Topics & Concepts
ChemistryArylPalladiumMoietyCatalysisCombinatorial chemistryYlideHydantoinPhosphineAlkylationOrganic chemistryAlkylChemical Synthesis and AnalysisCatalytic C–H Functionalization MethodsAdvanced Synthetic Organic Chemistry