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Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion

Erin E. Gray, Matthew K. Nielsen, Kimberly A. Choquette, Julia A. Kalow, Thomas J. A. Graham and Abigail G. Doyle*

*Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States, Email: agdoyleprinceton.edu

E. E. Gray, M. K. Nielsen, K. A. Choquette, J. A. Kalow, T. J. A. Graham, A. G. Doyle, J. Am. Chem. Soc., 2016, 138, 10802-10805.

DOI: 10.1021/jacs.6b06770


Abstract

A copper-catalyzed H-F insertion into α-diazocarbonyl compounds provides complex α-fluorocarbonyl derivatives under mild conditions using potassium fluoride (KF) and hexafluoroisopropanol. The method is readily adapted to radiofluorination with [18F]KF.

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Key Words

fluorination


ID: J48-Y2016