Abstract
AbstractSelective and efficient fluorination of organic 1,3‐dicarbonyl compounds was achieved using the electrophilic fluorinating reagents SelectfluorTM F‐TEDA‐BF4 (1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo[2.2.2]octane bis‐tetrafluoroborate) in aqueous medium or AccufluorTM NFSi (N‐fluorobenzenesulfonimide) under solvent‐free reaction conditions (SFRC). Under both reaction conditions cyclic 1,3‐dicarbonyl compounds were transformed into 2‐fluoro‐substituted derivatives and acyclic analogues into 2,2‐difluoro‐substituted compounds, while the reactions of 1‐trifluoromethyl‐substituted 1,3‐dicarbonyls in water resulted in the formation of 2,2‐difluoro‐3,3‐dihydroxy‐1‐one derivatives. The reactivity of the starting material in water was found to be dependent on its enolizability, hydrophobic interactions and aggregate state at the reaction temperature. Reactions under SFRC proceeded in the molten eutectic phase of the reactants. The technique of competitive reactivity was used in order to evaluate and better understand the effects of reaction conditions on the course of these reactions.
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