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dc.contributor.authorSiah, Huey-San Melanie
dc.contributor.authorFiksdahl, Anne
dc.date.accessioned2017-10-25T10:12:42Z
dc.date.available2017-10-25T10:12:42Z
dc.date.created2017-03-06T11:32:04Z
dc.date.issued2017
dc.identifier.citationJournal of fluorine chemistry. 2017, 197 24-33.nb_NO
dc.identifier.issn0022-1139
dc.identifier.urihttp://hdl.handle.net/11250/2462053
dc.description.abstractThe 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.isoengnb_NO
dc.publisherElseviernb_NO
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 Internasjonal*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/deed.no*
dc.titleDual-gold(I)-generated trifluoromethylation of terminal alkynes With Togni’s reagentnb_NO
dc.typeJournal articlenb_NO
dc.typePeer reviewednb_NO
dc.description.versionacceptedVersionnb_NO
dc.source.pagenumber24-33nb_NO
dc.source.volume197nb_NO
dc.source.journalJournal of fluorine chemistrynb_NO
dc.identifier.doi10.1016/j.jfluchem.2017.01.004
dc.identifier.cristin1455936
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.unitcode194,66,25,0
cristin.unitnameInstitutt for kjemi
cristin.ispublishedtrue
cristin.fulltextoriginal
cristin.qualitycode1


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Attribution-NonCommercial-NoDerivatives 4.0 Internasjonal
Except where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivatives 4.0 Internasjonal