Oxidative-substitution reactions of polycyclic aromatic hydrocarbons with iodine(III) sulfonate reagents

Polycyclic aromatic hydrocarbons (PAH) undergo regioselective oxidative-substitution reactions with iodine(III) sulfonate reagents in dichloromethane to give the corresponding aryl sulfonate esters. The use of [hydroxy(tosyloxy)iodo]benzene in conjunction with trimethylsilyl isothiocyanate leads to thiocyanation of the PAH nucleus.