Alkyne hydroarylation with Au N-heterocyclic carbene catalysts
Mono- and dinuclear gold complexes with N-heterocyclic carbene (NHC) ligands have been employed as catalysts in the intermolecular hydroarylation of alkynes with simple unfunctionalised arenes. Both mono- and dinuclear gold(III) complexes were able to catalyze the reaction; however, the best results...
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Beilstein-Institut
2013
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| Online Access: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3566786/ |
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pubmed-35667862013-02-11 Alkyne hydroarylation with Au N-heterocyclic carbene catalysts Tubaro, Cristina Baron, Marco Biffis, Andrea Basato, Marino Full Research Paper Mono- and dinuclear gold complexes with N-heterocyclic carbene (NHC) ligands have been employed as catalysts in the intermolecular hydroarylation of alkynes with simple unfunctionalised arenes. Both mono- and dinuclear gold(III) complexes were able to catalyze the reaction; however, the best results were obtained with the mononuclear gold(I) complex IPrAuCl. This complex, activated with one equivalent of silver tetrafluoroborate, exhibited under acidic conditions at room temperature much higher catalytic activity and selectivity compared to more commonly employed palladium(II) catalysts. Moreover, the complex was active, albeit to a minor extent, even under neutral conditions, and exhibited lower activity but higher selectivity compared to the previously published complex AuCl(PPh3). Preliminary results on intramolecular hydroarylations using this catalytic system indicate, however, that alkyne hydration by traces of water may become a serious competing reaction. Beilstein-Institut 2013-02-05 /pmc/articles/PMC3566786/ /pubmed/23400639 http://dx.doi.org/10.3762/bjoc.9.29 Text en Copyright © 2013, Tubaro et al; licensee Beilstein-Institut. http://www.beilstein-journals.org/bjoc This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc) |
| repository_type |
Open Access Journal |
| institution_category |
Foreign Institution |
| institution |
US National Center for Biotechnology Information |
| building |
NCBI PubMed |
| collection |
Online Access |
| language |
English |
| format |
Online |
| author |
Tubaro, Cristina Baron, Marco Biffis, Andrea Basato, Marino |
| spellingShingle |
Tubaro, Cristina Baron, Marco Biffis, Andrea Basato, Marino Alkyne hydroarylation with Au N-heterocyclic carbene catalysts |
| author_facet |
Tubaro, Cristina Baron, Marco Biffis, Andrea Basato, Marino |
| author_sort |
Tubaro, Cristina |
| title |
Alkyne hydroarylation with Au N-heterocyclic carbene catalysts |
| title_short |
Alkyne hydroarylation with Au N-heterocyclic carbene catalysts |
| title_full |
Alkyne hydroarylation with Au N-heterocyclic carbene catalysts |
| title_fullStr |
Alkyne hydroarylation with Au N-heterocyclic carbene catalysts |
| title_full_unstemmed |
Alkyne hydroarylation with Au N-heterocyclic carbene catalysts |
| title_sort |
alkyne hydroarylation with au n-heterocyclic carbene catalysts |
| description |
Mono- and dinuclear gold complexes with N-heterocyclic carbene (NHC) ligands have been employed as catalysts in the intermolecular hydroarylation of alkynes with simple unfunctionalised arenes. Both mono- and dinuclear gold(III) complexes were able to catalyze the reaction; however, the best results were obtained with the mononuclear gold(I) complex IPrAuCl. This complex, activated with one equivalent of silver tetrafluoroborate, exhibited under acidic conditions at room temperature much higher catalytic activity and selectivity compared to more commonly employed palladium(II) catalysts. Moreover, the complex was active, albeit to a minor extent, even under neutral conditions, and exhibited lower activity but higher selectivity compared to the previously published complex AuCl(PPh3). Preliminary results on intramolecular hydroarylations using this catalytic system indicate, however, that alkyne hydration by traces of water may become a serious competing reaction. |
| publisher |
Beilstein-Institut |
| publishDate |
2013 |
| url |
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3566786/ |
| _version_ |
1611953253138825216 |