S<sub>N</sub>Ar and C–H Amination of Electron Rich Arenes with Pyridine as a Nucleophile Using Photoredox Catalysis
Mark A. Mantell, Matthew R. Lasky, Melissa Lee, Matthew S. Remy, Melanie S. Sanford
Abstract
This report describes the development of two photocatalytic methods for the pyridination of electron rich arenes. First, an SNAr-type reaction between aryl halides and pyridine is developed and optimized. This transformation affords selective substitution of C(sp2)–halogen over C(sp2)–OR bonds to afford arylpyridinium products under anaerobic conditions. Under complementary aerobic conditions, analogous substrates are shown to undergo oxidative C(sp2)–H pyridination.
Topics & Concepts
ChemistryAminationPyridineNucleophilic aromatic substitutionPhotoredox catalysisNucleophileCatalysisArylHalogenPhotocatalysisPhotochemistryMedicinal chemistryHalideNucleophilic substitutionAryl halideCombinatorial chemistryOrganic chemistryPalladiumAlkylCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSynthesis and Catalytic Reactions