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, Abigail G. Doyle

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

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 [18F]KF. This late-stage strategy provides an attractive route to 18F-labeled biomolecules.

Original languageEnglish (US)
Pages (from-to)10802-10805
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number34
DOIs
StatePublished - Aug 31 2016

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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