Electrochemical Formation of Oxazolines by 1,3-Oxyfluorination of Non-activated Cyclopropanes.

The C-C bond in non-activated cyclopropanes can be intramolecularly cleaved with an electrochemically generated amidyl radical forming oxazolines. In the presence of TBABF, this provides 1,3-oxyfluorination products. C-C bond cleavage of cyclopropane proceeds with inversion of the configuration, suggesting an intramolecular homolytic substitution (Si) mechanism. The performance of TBABF as an efficient fluoride source was explained by accumulation of the BF anion at the anode surface, at which a carbocation is formed by the oxidation of the C-centered radical.