Chloroimidazolium Deoxyfluorination Reagent with HF Anion as a Sole Fluoride Source.

In the study, we introduce an air-stable NHC-based deoxyfluorination reagent ImCl[HF], offering a promising avenue for deoxyfluorination across various substrates. Reagent efficiently fluorinates benzyl alcohols, carboxylic acids, and P(V) compounds without external fluoride sources. A mechanistic study reveals a two-step process involving benzyl chloride as an intermediate, shedding light on the two-step reaction pathway. The Hammet plot provides insights into reaction mechanisms with different substrates, enhancing our understanding of this versatile deoxyfluorination method.