Diaryliodoniums by Rhodium(III)-Catalyzed C-H Activation: Mild Synthesis and Diversified Functionalizations.

Diaryliodonium salts play an increasingly important role as an aryl source. Reported is the first synthesis of diaryliodoniums by rhodium(III)-catalyzed C-H hyperiodination of electron-poor arenes under chelation assistance. This C-I coupling reaction occurred at room temperature with high regio-selectivity and functional-group compatibility. Subsequent diversified nucleophilic functionalization of a diaryliodonium allowed facile construction of C-C, C-N, C-O, C-S, C-P and C-Br bonds, and in all cases the initial functionalization occurred at the arene containing the chelating-group.