Wednesday, February 3, 2016

Regioselective Electrophilic Fluorination of Rationally Designed Imidazole Derivatives

Regioselective Electrophilic Fluorination of Rationally Designed Imidazole Derivatives

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.


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