Computational and Theoretical Chemistry
Computational and Theoretical Chemistry
4 years ago

Persulfate-promoted benzylic mono- and difluorination: A mechanistic study

Persulfate-promoted benzylic mono- and difluorination: A mechanistic study
A systematic investigation has been conducted into the mechanism for the persulfate-promoted benzylic mono- and difluorination with Selectfluor by using density functional theory (DFT). In the monofluorination, the role of SO4 − (from the substrate-assisted cleavage of S2O8 2 − in the initiation phase) is just to trigger fluorination by producing the initial benzyl radical. The cationic N-radical from the fluorine transfer between the benzyl radical and Selectfluor can abstract hydrogen from the substrate, generating the benzyl radical to complete the reaction cycle. The difluorination contains the monofluorination and the second fluorine transfer. The benzylic CH activation in the monofluorination product can be achieved by cationic N-radical or SO4 − . Whether in monofluorination or in difluorination, the rate-determining step is the generation of SO4 −.

Publisher URL: www.sciencedirect.com/science

DOI: S2210271X17304115

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