A SHORT-CUT SYNTHESIS OF DIARYLIODONIUM BROMIDES FOLLOWED BY OXIDATIVE ANION METATHESES

This paper reports a one-pot synthesis of the title bromides (in 20-88% crude yields) from iodoarenes oxidized with the CrO3/ AcOH/Ac2O/H2SO4 liquid mixture, then coupled in situ with arenes and, finally, precipitated out with a KBr solution. Similarly, diaryliodonium perchlorates and iodides are obtained in 40-89% crude yields. Oxidative anion metatheses in the crude title bromides produce the respective pure diaryliodonium tetrafluoroborates, tosylates, trifluoroacetates, hydrosulfates, nitrates, and chlorides in 57-80% yields. These new preparative procedures are easier and shorter than many earlier methods.