Klaus Albertshofer* and Neelakandha S. Mani
Janssen Research & Development, LLC, 3210 Merryfield Row, San Diego, California 92121, United States
DOI: 10.1021/acs.joc.5b02592
J. Org. Chem.
Abstract:
We report the regioselective and direct functionalization of
rationally designed imidazole derivatives through electrophilic fluorina-
tion 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.
TOC:
