CATALYTIC COUPLING OF ARENES WITH p-IODONITROBENZENE IN A SYSTEM CONTAINING ArH, ArI, PtII, 50% AQUEOUS KOH, AND 18-CROWN-6

The phenanthroline complex, Pt(phen)Cl2, catalyzes the coupling of aromatic hydrocarbons with p-iodonitrobenzene under phase transfer conditions using 50% aqueous KOH and 18-crown-6. The yield of the asymmetric diaryl products is 10,000-12,000% relative to the catalyst. A mechanism was proposed involving the oxidative addition of ArI to an Ar—PtII intermediate species with subsequent reductive elimination of the final product Ar—Ar´ from Ar—Pt^IV—Ar´.