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

ABSTRACT: The copper-catalyzed H-F insertion into α-diazocarbonyl compounds is described using potassium fluoride (KF) and hexafluoroisopropanol. Access to complex α-fluorocarbonyl derivatives is achieved under mild conditions, and the method is readily adapted to radiofluorination with [(18)F]KF. This late-stage strategy provides an attractive route to (18)F-labeled biomolecules.

SUBMITTER: Gray EE

PROVIDER: S-EPMC9011916 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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

Gray Erin E EE Nielsen Matthew K MK Choquette Kimberly A KA Kalow Julia A JA Graham Thomas J A TJ Doyle Abigail G AG

Journal of the American Chemical Society 20160817 34

The copper-catalyzed H-F insertion into α-diazocarbonyl compounds is described using potassium fluoride (KF) and hexafluoroisopropanol. Access to complex α-fluorocarbonyl derivatives is achieved under mild conditions, and the method is readily adapted to radiofluorination with [(18)F]KF. This late-stage strategy provides an attractive route to (18)F-labeled biomolecules. ...[more]

PMID: 27500313

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