Advanced search
Add to list

Hydrofluorination of alkynes catalysed by gold bifluorides

(2015) CHEMCATCHEM. 7(2). p.240-244
Author
Organization
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.
Keywords
alkynes, bifluorides, gold, hydrofluorination, carbenes, C-H FLUORINATION, COPPER-MEDIATED FLUORINATION, NUCLEOPHILIC FLUORINATION, UNACTIVATED ALKENES, FLUORIDE COMPLEX, BOND ACTIVATION, ARYL BROMIDES, REACTIVITY, LIGANDS, REAGENT

Citation

Please use this url to cite or link to this publication:

MLA
Nahra, Fady et al. “Hydrofluorination of Alkynes Catalysed by Gold Bifluorides.” CHEMCATCHEM 7.2 (2015): 240–244. Print.
APA
Nahra, F., Patrick, S. R., Bello, D., Brill, M., Obled, A., Cordes, D. B., Slawin, A. M., et al. (2015). Hydrofluorination of alkynes catalysed by gold bifluorides. CHEMCATCHEM, 7(2), 240–244.
Chicago author-date
Nahra, Fady, Scott R Patrick, Davide Bello, Marcel Brill, Alan Obled, David B Cordes, Alexandra MZ Slawin, David O’Hagan, and Steven Nolan. 2015. “Hydrofluorination of Alkynes Catalysed by Gold Bifluorides.” Chemcatchem 7 (2): 240–244.
Chicago author-date (all authors)
Nahra, Fady, Scott R Patrick, Davide Bello, Marcel Brill, Alan Obled, David B Cordes, Alexandra MZ Slawin, David O’Hagan, and Steven Nolan. 2015. “Hydrofluorination of Alkynes Catalysed by Gold Bifluorides.” Chemcatchem 7 (2): 240–244.
Vancouver
1.
Nahra F, Patrick SR, Bello D, Brill M, Obled A, Cordes DB, et al. Hydrofluorination of alkynes catalysed by gold bifluorides. CHEMCATCHEM. 2015;7(2):240–4.
IEEE
[1]
F. Nahra et al., “Hydrofluorination of alkynes catalysed by gold bifluorides,” CHEMCATCHEM, vol. 7, no. 2, pp. 240–244, 2015.
@article{8168399,
  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.},
  author       = {Nahra, Fady and Patrick, Scott R and Bello, Davide and Brill, Marcel and Obled, Alan and Cordes, David B and Slawin, Alexandra MZ and O'Hagan, David and Nolan, Steven},
  issn         = {1867-3880},
  journal      = {CHEMCATCHEM},
  keywords     = {alkynes,bifluorides,gold,hydrofluorination,carbenes,C-H FLUORINATION,COPPER-MEDIATED FLUORINATION,NUCLEOPHILIC FLUORINATION,UNACTIVATED ALKENES,FLUORIDE COMPLEX,BOND ACTIVATION,ARYL BROMIDES,REACTIVITY,LIGANDS,REAGENT},
  language     = {eng},
  number       = {2},
  pages        = {240--244},
  title        = {Hydrofluorination of alkynes catalysed by gold bifluorides},
  url          = {http://dx.doi.org/10.1002/cctc.201402891},
  volume       = {7},
  year         = {2015},
}

Altmetric
View in Altmetric
Web of Science
Times cited: