A Unified Strategy to access N-Heterocycles Enabled by Hypervalent Iodine(III) Reagent Mediated Imidate Radical Cyclization

Abstract

We report a unified strategy utilizing bench stable hypervalent iodine(III) reagent in the construction of phenanthridine, isoquinoline, quinoline and pyridine from aryl/alkenyl imidates. Mechanistic studies revealed the involvement of imidate radical intermediates, which undergoes intramolecular homolytic aromatic substitution (HAS) to give range of heteroarenes. The reaction can also be extended to the gram scale synthesis and exhibits high functional group tolerance to offers an efficient alternative for the construction of N-containing arenes.