Hydrofluorination of alkynes catalysed by gold bifluorides

F. Nahra, S.R. Patrick, D. Bello, M. Brill, A. Obled, D.B. Cordes, A.M.Z. Slawin, D. O'Hagan, S.P. Nolan

Research output: Contribution to journalArticlepeer-review

83 Citations (Scopus)

Abstract

We report the synthesis of nine new N-heterocyclic carbene gold bifluoride complexes starting from the corresponding N-heterocyclic carbene gold hydroxides. A new methodology to access N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene gold(I) fluoride starting from N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene gold(I) hydroxide and readily available potassium bifluoride is also reported. These gold bifluorides were shown to be efficient catalysts in the hydrofluorination of symmetrical and unsymmetrical alkynes, thus affording fluorinated stilbene analogues and fluorovinyl thioethers in good to excellent yields with high stereo- and regioselectivity. The method is exploited further to access a fluorinated combretastatin analogue selectively in two steps starting from commercially available reagents.
Original languageEnglish
Pages (from-to)240-244
Number of pages5
JournalChemCatChem
Volume7
Issue number2
Early online date26 Nov 2014
DOIs
Publication statusPublished - Jan 2015

Keywords

  • Alkynes
  • Bifluorides
  • Gold
  • Hydrofluorination
  • Carbenes

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