A variety of N-heterocyclic derivatives were synthesized by iodine-mediated aminative difunctionalization/cyclization of N-alkenyl sulfonamides involving nitrogen-centered radicals. Governed by the disulfide/diselenide reagent, the synthesis delivers either iodinated N-heterocyclic products (in the absence of these reagents) or thiolated/selenylated products (in their presence).

Abstract

A variety of N-heterocyclic derivatives were synthesized by iodine-mediated aminative difunctionalization/cyclization of N-alkenyl sulfonamides. The present synthetic process involves nitrogen-centered radicals generated from sulfonamide precursors. It is operationally simple and amenable to gram-scale synthesis under transition-metal-free conditions. The reaction is applicable to the synthesis of iodinated N-heterocyclic products in the absence of disulfides/diselenides and also to the preparation of thiolated/selenylated products in their presence, respectively.