An efficient p-thiocyanation of phenols and naphthols using a reagent combination of phenyliodine dichloride and lead(II) thiocyanate

Article abstract of DOI:10.1248/cpb.45.1887

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.