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Experimental and Theoretical Evidence for Nitrogen-Fluorine Halogen Bonding in Silver-Initiated Radical Fluorinations
We
report experimental and computational evidence for nitrogen–fluorine
halogen bonding in AgÂ(I)-initiated radical C–H fluorinations.
Simple pyridines form [N–F–N]+ halogen bonds
with Selectfluor to facilitate single-electron reduction by catalytic
AgÂ(I). Pyridine electronics affect the extent of halogen bonding,
leading to significant differences in selectivity between mono- and
difluorinated products. Electronic structure calculations show that
halogen bonding to various pyridines alters the single-electron reduction
potential of Selectfluor, which is consistent with experimental electrochemical
analysis. Multinuclear correlation NMR also provides spectroscopic
evidence for pyridine halogen bonding to Selectfluor under ambient
conditions