Catalytic fluorination of 1,3-dicarbonyl compounds using iodoarene catalysts

Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization

“…This step was not considered explicitly by the calculations, but the formation of ( R , R ) -1c-F 2 is supported by experiments that confirm the oxidation of iodoarene by m CPBA to form the iodosylarene (ArI=O), which is readily converted to the difluorinated species by reaction with HF. 35 , 71 − 73 …”

Iodine‐Catalyzed Oxidative Coupling Reactions Utilizing CH and XH as Nucleophiles

“…In 2013, Kitamura and co-workers revealed an iodoarene-catalyzed fluorination of 1,3-dicarbonyl compounds. [73] m-CPBA provedt ob ea no ptimal oxidant and aqueous HF acted as an efficient fluorine source. Different substituted 2-fluoro-1,3-dicarbonyl compounds could be obtained in good yields [Eq.…”

“…In 2013, Kitamura and co‐workers revealed an iodoarene‐catalyzed fluorination of 1,3‐dicarbonyl compounds 73 . m ‐CPBA proved to be an optimal oxidant and aqueous HF acted as an efficient fluorine source.…”

Kitamura Electrophilic Fluorination Using HF as a Source of Fluorine

“…Considering the postulated reaction mechanism (Scheme 2) involving eventual transformation (reduction) of iodosylbenzene to iodobenzene 10, the final reaction product, the authors posited that providing in situ efficient oxidation of the latter to iodosylbenzene, would allow for a catalytic version of this process. Indeed, a significant breakthrough was made with the application of m-CPBA as a terminal oxidant [109]. As presented in Scheme 5, the Ar-I, used in catalytic amounts, undergoes a three-step transformation: oxidation to Ar-IO, reaction with HF to produce Ar-IF 2 and reaction with the enolate form of 15 giving rise to the target product 16. of the corresponding fluorinated products 16 are a bit lower (~50-70%), likely due to possible enolization.…”