Palladium-catalyzed intramolecular redox-relay Heck cyclization: access to heterocycles bearing all-carbon quaternary centers

Abstract

While the intramolecular Heck reaction of aryl/vinyl halides with various alkenes has been well studied, the exploration of acyclic alkenol systems via a redox-relay strategy remains unexploited. Herein, we disclose the first palladium-catalyzed intramolecular redox-relay Heck cyclization of vinyl/aryl iodides with alkenols for establishing heterocyclic all-carbon quaternary centers. Diverse 5–7-membered (benzo)heterocycles with a remote carbonyl functionality are obtained in good to excellent yields using a bipyridine ligand. Moreover, an asymmetric version of this transformation could be realized in good yield with promising enantioselectivity.