Fluorohydroxylation and Hydration Reactions of para-Quinone Methides Promoted by Selectfluor

Abstract

Selectfluor-promoted vicinal fluorohydroxylation and hydration reaction of para-quinone methides (p-QMs) were described, affording vicinal fluorohydrins and ketone/ether products in high yields. The hydration products were highly controlled by the electronic properties of substituents in the aromatic ring, and simultaneously, the amount of Selectfluor was completely different during the synthesis of ketone/ether products. This reaction also represents the first fluorohydroxylation of p-QMs, and the wide range of p-QMs makes the vicinal fluorohydroxylation of great significance.