S_NAr and C–H Amination of Electron Rich Arenes with Pyridine as a Nucleophile Using Photoredox Catalysis

Abstract

This report describes the development of two photocatalytic methods for the pyridination of electron rich arenes. First, an S_NAr-type reaction between aryl halides and pyridine is developed and optimized. This transformation affords selective substitution of C(<i>sp</i>²)-halogen over C(<i>sp</i>²)-OR bonds to afford arylpyridinium products under anaerobic conditions. Under complementary aerobic conditions, analogous substrates are shown to undergo oxidative C(<i>sp</i>²)-H pyridination.