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

Abstract

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 4 , this provides 1,3-oxyfluorination products. C−C bond cleavage of cyclopropane proceeds with inversion of the configuration, suggesting an intramolecular homolytic substitution (S H i) mechanism. The performance of TBABF 4 as an efficient fluoride source was explained by accumulation of the BF 4 − anion at the anode surface, at which a carbocation is formed by the oxidation of the C-centered radical.