dc.contributor.author | Siah, Huey-San Melanie | |
dc.contributor.author | Fiksdahl, Anne | |
dc.date.accessioned | 2017-10-25T10:12:42Z | |
dc.date.available | 2017-10-25T10:12:42Z | |
dc.date.created | 2017-03-06T11:32:04Z | |
dc.date.issued | 2017 | |
dc.identifier.citation | Journal of fluorine chemistry. 2017, 197 24-33. | nb_NO |
dc.identifier.issn | 0022-1139 | |
dc.identifier.uri | http://hdl.handle.net/11250/2462053 | |
dc.description.abstract | The interaction of a Au(I) catalyst (JohnPhosAu(I)-MeCN/SbF6) and the Togni’s reagent 1, as a source of electrophilic trifluoromethyl group, has been studied in order to develop gold-catalysed alkyne trifluoromethylation reactions. Alkyne-CF3 products were prepared in moderate yields (up to 46%) by electrophilic trifluoromethylation of terminal arylalkynes with Togni’s reagent 1 in the presence of sub-stoichiometric amounts of gold catalyst (25%). The proposed addition-elimination reaction mechanism proceeds through a Au-Togni Reagent complex with a linear Togni Reagent-O-Au(I)-P-(phosphane) coordination mode (X-ray analysis). Alkyne deprotonation gives rapid formation of protonated Togni Reagent and a σ,π-acetylide dual-Au complex, confirmed by X-ray analysis. It was shown that the σ,π-dual-Au complex activates for trifluoromethylation, most likely by transfer of a [LAu]+ fragment to the alkyne substrate. The resulting reactive π-Au+-alkyne intermediate probably undergoes O-/CF3-addition of Togni Reagent, and final elimination of Togni alcohol gives the alkyne-CF3 product. | nb_NO |
dc.language.iso | eng | nb_NO |
dc.publisher | Elsevier | nb_NO |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internasjonal | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/deed.no | * |
dc.title | Dual-gold(I)-generated trifluoromethylation of terminal alkynes With Togni’s reagent | nb_NO |
dc.type | Journal article | nb_NO |
dc.type | Peer reviewed | nb_NO |
dc.description.version | acceptedVersion | nb_NO |
dc.source.pagenumber | 24-33 | nb_NO |
dc.source.volume | 197 | nb_NO |
dc.source.journal | Journal of fluorine chemistry | nb_NO |
dc.identifier.doi | 10.1016/j.jfluchem.2017.01.004 | |
dc.identifier.cristin | 1455936 | |
dc.description.localcode | © 2017. This is the authors’ accepted and refereed manuscript to the article. LOCKED until 11.1.2019 due to copyright restrictions. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ | nb_NO |
cristin.unitcode | 194,66,25,0 | |
cristin.unitname | Institutt for kjemi | |
cristin.ispublished | true | |
cristin.fulltext | original | |
cristin.qualitycode | 1 | |