Palladium-Catalyzed Cross-Electrophile Coupling between Aryl Diazonium Salt and Aryl Iodide/Diaryliodonium Salt in H2O–EtOH

We report herein a mild highly chemoselective palladium-catalyzed cross-electrophile coupling between readily accessible aromatic diazonium salt and aryl iodide or diaryliodonium salt in water–ethanol (2:1) medium. Mechanistic studies revealed that ethanol is crucial to generate an active Pd(0) catalyst, and the counterion of the diazonium salt renders a cationic Pd(II) species that facilitates subsequent oxidative addition to aryl iodide/diaryliodonium salt. Silver(I) salt was crucial to retain the catalytic activity of palladium, removing the iodide ion as a precipitate.