A study towards the undirected fluorination and chlorination of cubane 1,4-diester
Laly Donnier-Valentin1, Robin Heinrich1, Quentin Fevre-Renault1,2
1Univ Rouen Normandie, INSA Rouen Normandie, Univ Caen Normandie, ENSICAEN, CNRS, Institut CARMeN UMR 6064, 76000 Rouen, France.
Abstract:
A study towards the undirected C-H fluorination and chlorination of cubane 1,4-diester is described using a user-friendly reagent such as Selectfluor and 1,3-dichloro-5,5-dimethylhydantoin under photoinduction. While the fluorocubane 1,4-diester is formed in low yield (8% yield) due to loss of material, the chlorocubane 1,4-diester was on the other hand prepared in 59% yield without the need for any photocatalyst. Moreover, a proof-of-concept of the chlorination of this strained scaffold was demonstrated using flow technology.
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