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Chloroimidazolium Deoxyfluorination Reagent with H2F3- Anion as a Sole Fluoride Source
Griša Prinčič1, Blaž Omahen1, Jan Jelen2
1Department of Chemistry and Biochemistry, Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia.
Abstract:
In the study, we introduce an air-stable NHC-based deoxyfluorination reagent ImCl[H2F3], 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.
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