Rapid preparation of fluorinated aromatic heterocycles

Haoran Sun, Andrew S. Koch, Stephen G. DiMagno

Research output: Chapter in Book/Report/Conference proceedingConference contribution

1 Scopus citations

Abstract

Nucleophilic aromatic substitution (SNAr) reactions are typically used for fluoride introduction into heterocyclic aromatic compounds, but substitution occurs sluggishly with unactivated substrates. This chapter discusses new reagents and methods for fluorination of key heterocyclic pharmacophores. Purines, pyrimidines, pyridines, and even imidazoles are fluorinated readily with anhydrous tetralkylammonium fluorides in DMSO. Though the tetraalkylammonium fluoride reagents themselves are prone to decomposition, the presence of substrate protects these fragile reagents and permits rapid fluorination of relatively reluctant substrates at high temperature. Use of anhydrous fluorinating reagents in radiochemistry is facilitated by a fluoride-relay process that quickly converts hydrated potassium fluoride into anhydrous, exceptionally nucleophilic tetraalkylammonium fluorides.

Original languageEnglish (US)
Title of host publicationFluorinated Heterocycles
PublisherAmerican Chemical Society
Pages85-104
Number of pages20
ISBN (Print)9780841269538
StatePublished - Jan 1 2009

Publication series

NameACS Symposium Series
Volume1003
ISSN (Print)0097-6156
ISSN (Electronic)1947-5918

    Fingerprint

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Sun, H., Koch, A. S., & DiMagno, S. G. (2009). Rapid preparation of fluorinated aromatic heterocycles. In Fluorinated Heterocycles (pp. 85-104). (ACS Symposium Series; Vol. 1003). American Chemical Society.