Deacetylative Aryl Migration of Diaryliodonium Salts with C(sp2)-N Bond Formation toward ortho-Iodo N-Aryl Sulfonamides.

Abstract

An unprecedented approach of metal-free C(sp2)-N bond formation via deacetylation/intramolecular aryl migration is demonstrated with novel N-sulfonamide substituted diaryliodonium salts. The reaction provides a variety of ortho-iodo N-aryl sulfonamides. The products were employed in several coupling reactions to afford useful diarylamine scaffolds. Furthermore, the key intermediates of zwitterionic iodoniums in the reaction were isolated and verified by the X-ray crystallographic analysis, which showcased unambiguous mechanistic insight into the reactivity of the reaction cascade.