We report experimental and computational {evidence|proof} for nitrogen–fluorine halogen bonding in Ag(I)-initiated radical C–H fluorinations. {Simple|Easy|Straightforward|Basic|Uncomplicated|Very simple} pyridines {form|type|kind} [N–F–N]+ halogen bonds with Selectfluor to facilitate single-electron reduction by catalytic Ag(I). Pyridine electronics {affect|impact|have an effect on|influence} the extent of halogen bonding, {leading|top|major} to notable {differences|variations} in selectivity {between|in between|among|amongst|involving} mono- and bis-fluorinated {products|goods|items|merchandise|solutions}. Electronic structure calculations show that halogen bonding to {various|numerous|different|a variety of|several|many} pyridines alters the single-electron reduction {potential|possible|prospective} of Selectfluor, {which is|that is|which can be} {consistent|constant} with experimental electrochemical {analysis|evaluation}. Multinuclear correlation NMR also {provides|offers|gives|supplies|delivers} spectroscopic {evidence|proof} for pyridine halogen bonding to Selectfluor {under|below|beneath} ambient {conditions|circumstances|situations}. 1-Bromo-4-(trifluoromethyl)benzene site 3-Methoxy-1H-indole Price PMID:32472497
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