Hydrofluorination of alkynes catalysed by gold bifluorides
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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.
Nahra , F , Patrick , S R , Bello , D , Brill , M , Obled , A , Cordes , D B , Slawin , A M Z , O'Hagan , D & Nolan , S P 2015 , ' Hydrofluorination of alkynes catalysed by gold bifluorides ' ChemCatChem , vol. 7 , no. 2 , pp. 240-244 . DOI: 10.1002/cctc.201402891
Copyright 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
DescriptionThe ERC (Advanced Investigator Award FUNCAT and PoC award GOLDCAT), the EPSRC and Syngenta are gratefully acknowledged for support of this work. Umicore AG is acknowledged for their generous gift of auric acid. S.P.N. is a Royal Society Wolfson Research Merit Award holder.
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