Mono- and trifluorination of the thiazole ring of 2,5-diarylthiazoles using N-fluorobenzenesulfonimide (NFSI)

Julie M. Hatfield, Cheryl K Eidell, Chad E. Stephens

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Fluorination of select 2,5-diarylthiazoles using the N-F reagent N-fluorobenzenesulfonimide (NFSI) has led to the formation of both the anticipated 4-fluorothiazole as well as a unique 4,4,5-trifluorothiazole. Selective monofluorination is best achieved using bromobenzene as solvent at 155 °C, while trifluorination is best achieved by performing the reaction without solvent at 135-140 °C. An X-ray crystal structure has been obtained on one of the trifluorinated products.

Original languageEnglish (US)
Pages (from-to)1025-1028
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number8
DOIs
StatePublished - Feb 20 2013

Fingerprint

Thiazoles
Fluorination
Halogenation
Crystal structure
X-Rays
X rays
N-fluorobenzenesulfonimide
bromobenzene

Keywords

  • Fluorination
  • N-F reagents
  • NFSI
  • Solvent free reaction
  • Thiazole

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Mono- and trifluorination of the thiazole ring of 2,5-diarylthiazoles using N-fluorobenzenesulfonimide (NFSI). / Hatfield, Julie M.; Eidell, Cheryl K; Stephens, Chad E.

In: Tetrahedron Letters, Vol. 54, No. 8, 20.02.2013, p. 1025-1028.

Research output: Contribution to journalArticle

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AU - Stephens, Chad E.

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