A unified strategy to access N-heterocycles enabled by hypervalent iodine(iii) reagent-mediated imidate radical cyclization

Abstract

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