An Efficient p-Thiocyanation of Phenols and Naphthols Using a Reagent Combination of Phenyliodine Dichloride and Lead(II) Thiocyanate.

A combination of PhICl2 and Pb(SCN)2 is effective for the p-selective thiocyanation of various types of p-unsubstituted phenols and naphthols 1 to give p-thiocyanatophenols and naphthols 3. The reaction proceeded at 0°C to room temperature in good to quantitative yields. Twenty-five examples are given, in which various functional groups, such as chloro, allyl, carbonyl, ester, amide, and primary hydroxyl groups, are shown to be compatible with this reaction.