Hydrofluorination of Alkynes Catalysed by Gold Bifluorides

• DOI: 10.1002/cctc.201402891
• Publication Date: 2014-11-26T20:58:17Z
• Authors: Fady Nahra; Scott R. Patrick; Davide Bello; Marcel Brill; Alan Obled; David B. Cordes; Alexandra M. Z. S...; David O'Hagan; Steven P. Nolan
• Keywords: Bifluorides; Hydrofluorination; 500; DAS; 540; QD Chemistry; 01 natural sciences; Communications; 0104 chemical sciences; Alkynes; Carbenes; QD; Gold

We report the synthesis of nine new N-heterocyclic carbene gold bifluoride complexes starting from corresponding hydroxides. A methodology to access N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene gold(I) fluoride hydroxide and readily available potassium is also reported. These bifluorides were shown be efficient catalysts in hydrofluorination symmetrical unsymmetrical alkynes, thus affording fluorinated stilbene analogues fluorovinyl thioethers good excellent yields with high stereo- regioselectivity. The method exploited further a combretastatin analogue selectively two steps commercially reagents.