Journal
CHEMCATCHEM
Volume 7, Issue 2, Pages 240-244Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201402891
Keywords
alkynes; bifluorides; gold; hydrofluorination; carbenes
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Funding
- ERC (Advanced Investigator Award FUNCAT)
- ERC (PoC award GOLDCAT)
- EPSRC
- Syngenta
- Royal Society Wolfson Research Merit Award
- EPSRC [EP/J011053/1, EP/K039210/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K039210/1, EP/J011053/1] Funding Source: researchfish
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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.
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