Fluorohydrin Synthesis via Formal C–H Fluorination of Cyclic Alcohols

Installation of C-F bonds, particularly at the expense of C-H bonds, is of exceptional importance in the development of pharmaceuticals, agrochemicals, and advanced materials. Toward introducing this moiety, here we show that cyclic fluorohydrins can be directly generated via formal C-H fluorination of 5-, 6-, 7-, and 8-membered cyclic alcohols using Selectfluor. Mechanistic studies are consistent with fluorohydrin formation via an ionic elimination-hydroxyfluorination cascade proceeding through an alkene intermediate.