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Wiley, ChemCatChem, 2(7), p. 240-244, 2014

DOI: 10.1002/cctc.201402891

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Hydrofluorination of Alkynes Catalysed by Gold Bifluorides

Journal article published in 2014 by Fady Nahra ORCID, Scott R. Patrick, Davide Bello, Marcel Brill, Alan Obled, David B. Cordes, Alexandra M. Z. Slawin ORCID, David O'Hagan, Steven P. Nolan ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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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.