About: Experimental and Theoretical Study of Hoveyda-Grubbs Catalysts Modified by Perfluorohexyl Ponytail in the Alkoxybenzylidene Ligand.

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About: Experimental and Theoretical Study of Hoveyda-Grubbs Catalysts Modified by Perfluorohexyl Ponytail in the Alkoxybenzylidene Ligand. Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	The alkoxybenzylidene ligand of Hoveyda-Grubbs 1st and 2nd generation catalysts was modified with one or two perfluorohexyl groups by Ullmann reaction with the aim to improve both the fluorophilicity and activity of the catalyst. While bis(perfluorohexylation) resulted in inability of the ligand to exchange tricyclohexylphosphine ligand of parent Grubbs catalysts, mono(perfluorohexylation) and subsequent ligand exchange resulted in the formation of complexes of light fluorous properties and substantially higher activity in model RCM reactions. Modification of the mesityl group of the unsaturated NHC ligandby polyfluoroalkyl ponytails resulted in the formation of ruthenium precatalyst furnishing active catalytic intermediate with light fluorous properties. DFT computations of the model initiation reaction of ethene with Hoveyda-Grubbs 2nd generation catalyst or its pentafluoroethylated counterpart revealed that in the latter, the intermediate ruthenacyclobutane can form and decompose with significantly lower energies, thus explaining its higher activity. The alkoxybenzylidene ligand of Hoveyda-Grubbs 1st and 2nd generation catalysts was modified with one or two perfluorohexyl groups by Ullmann reaction with the aim to improve both the fluorophilicity and activity of the catalyst. While bis(perfluorohexylation) resulted in inability of the ligand to exchange tricyclohexylphosphine ligand of parent Grubbs catalysts, mono(perfluorohexylation) and subsequent ligand exchange resulted in the formation of complexes of light fluorous properties and substantially higher activity in model RCM reactions. Modification of the mesityl group of the unsaturated NHC ligandby polyfluoroalkyl ponytails resulted in the formation of ruthenium precatalyst furnishing active catalytic intermediate with light fluorous properties. DFT computations of the model initiation reaction of ethene with Hoveyda-Grubbs 2nd generation catalyst or its pentafluoroethylated counterpart revealed that in the latter, the intermediate ruthenacyclobutane can form and decompose with significantly lower energies, thus explaining its higher activity. (en)
Title	Experimental and Theoretical Study of Hoveyda-Grubbs Catalysts Modified by Perfluorohexyl Ponytail in the Alkoxybenzylidene Ligand. Experimental and Theoretical Study of Hoveyda-Grubbs Catalysts Modified by Perfluorohexyl Ponytail in the Alkoxybenzylidene Ligand. (en)
skos:prefLabel	Experimental and Theoretical Study of Hoveyda-Grubbs Catalysts Modified by Perfluorohexyl Ponytail in the Alkoxybenzylidene Ligand. Experimental and Theoretical Study of Hoveyda-Grubbs Catalysts Modified by Perfluorohexyl Ponytail in the Alkoxybenzylidene Ligand. (en)
skos:notation	RIV/60461373:22310/13:43896817!RIV14-GA0-22310___
http://linked.open...avai/riv/aktivita	I P
http://linked.open...avai/riv/aktivity	I, P(GAP207/10/1533)
http://linked.open...iv/cisloPeriodika	červen
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Kelbichová, Vendula Schindler, Martin Babuněk, Mario Kvíčalová, Magdalena Kvíčala, Jaroslav Rybáčková, Markéta
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Fakulta chemické technologie
http://linked.open...dnocenehoVysledku	74012
http://linked.open...ai/riv/idVysledku	RIV/60461373:22310/13:43896817
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	DFT; Alkene metathesis; Fluorous; Ruthenium complex; NHC ligand; Hoveyda-Grubbs catalyst (en)
http://linked.open.../riv/klicoveSlovo	NHC ligand Alkene metathesis Fluorous Ruthenium complex Hoveyda-Grubbs catalyst DFT
http://linked.open...odStatuVydavatele	CH - Švýcarská konfederace
http://linked.open...ontrolniKodProRIV	[292A3184B566]
http://linked.open...i/riv/nazevZdroje	Journal of Fluorine Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	6 (xsd:int)
http://linked.open...cetTvurcuVysledku	8 (xsd:int)
http://linked.open...vavai/riv/projekt	Fluorous carbenes, complexes and ionic liquids based on perfluoropolyether-substituted imidazolium salts and their applications
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	153
http://linked.open...iv/tvurceVysledku	Cvačka, Josef Kvíčalová, Magdalena Schindler, Martin Kvíčala, Jaroslav Březinová, Anna Rybáčková, Markéta Babuněk, Mario Kelbichová, Vendula
http://linked.open...ain/vavai/riv/wos	000322940700003
issn	0022-1139
number of pages	13 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.jfluchem.2013.06.001
http://localhost/t...ganizacniJednotka	22310

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