title: Hydrofluorination of Alkynes Catalysed by Gold Bifluorides.
abstract: We report the synthesis of nine newN-heterocyclic carbene gold bifluoride complexes starting from the correspondingN-heterocyclic carbene gold hydroxides. A new methodology to accessN,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene gold(I) fluoride starting fromN,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.
authors.affiliation: EaStCHEM School of Chemistry, University of St Andrews St Andrews, KY16 9ST (UK).
authors.forename: Fady
authors.initials: F
authors.lastname: Nahra
authors.affiliation: EaStCHEM School of Chemistry, University of St Andrews St Andrews, KY16 9ST (UK).
authors.forename: Scott R
authors.initials: SR
authors.lastname: Patrick
authors.affiliation: EaStCHEM School of Chemistry, University of St Andrews St Andrews, KY16 9ST (UK).
authors.forename: Davide
authors.initials: D
authors.lastname: Bello
authors.affiliation: EaStCHEM School of Chemistry, University of St Andrews St Andrews, KY16 9ST (UK).
authors.forename: Marcel
authors.initials: M
authors.lastname: Brill
authors.affiliation: EaStCHEM School of Chemistry, University of St Andrews St Andrews, KY16 9ST (UK).
authors.forename: Alan
authors.initials: A
authors.lastname: Obled
authors.affiliation: EaStCHEM School of Chemistry, University of St Andrews St Andrews, KY16 9ST (UK).
authors.forename: David B
authors.initials: DB
authors.lastname: Cordes
authors.affiliation: EaStCHEM School of Chemistry, University of St Andrews St Andrews, KY16 9ST (UK).
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.affiliation: EaStCHEM School of Chemistry, University of St Andrews St Andrews, KY16 9ST (UK).
authors.forename: David
authors.initials: D
authors.lastname: O'Hagan
authors.affiliation: EaStCHEM School of Chemistry, University of St Andrews St Andrews, KY16 9ST (UK).
authors.forename: Steven P
authors.initials: SP
authors.lastname: Nolan
keywords: alkynes; bifluorides; carbenes; gold; hydrofluorination