jo5b02592_si_001.pdf (2.63 MB)
Regioselective Electrophilic Fluorination of Rationally Designed Imidazole Derivatives
journal contribution
posted on 2016-02-04, 15:53 authored by Klaus Albertshofer, Neelakandha S. ManiWe
report the regioselective and direct functionalization of rationally
designed imidazole derivatives through electrophilic fluorination
with N-fluorobenzenesulfonimide enabled via in situ
deprotonation with lithium 2,2,6,6-tetramethylpiperidine. Aided by
a controlled protecting group switch, we were able to effectively
target both the reactive 5- as well as the difficult to target 4-position
of these molecules, leading to a series of fluorinated polysubstituted
imidazoles in gram scale.