Experimental and theoretical study of Hoveyda-Grubbs catalysts modified by perfluorohexyl ponytail in the alkoxybenzylidene ligand

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F13%3A00396359" target="_blank" >RIV/61388963:_____/13:00396359 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22310/13:43896817

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.jfluchem.2013.06.001" target="_blank" >http://dx.doi.org/10.1016/j.jfluchem.2013.06.001</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.jfluchem.2013.06.001" target="_blank" >10.1016/j.jfluchem.2013.06.001</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Experimental and theoretical study of Hoveyda-Grubbs catalysts modified by perfluorohexyl ponytail in the alkoxybenzylidene ligand

Popis výsledku v původním jazyce

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 ligand by 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 w

Název v anglickém jazyce

Experimental and theoretical study of Hoveyda-Grubbs catalysts modified by perfluorohexyl ponytail in the alkoxybenzylidene ligand

Popis výsledku anglicky

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 ligand by 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 w

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/GAP207%2F10%2F1533" target="_blank" >GAP207/10/1533: Fluorové karbeny, komplexy a iontové kapaliny na bázi perfluorpolyethery substituovaných imidazoliových solí a jejich aplikace</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Fluorine Chemistry

ISSN

0022-1139

e-ISSN

—

Svazek periodika

153

Číslo periodika v rámci svazku

September

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

14

Strana od-do

12-25

Kód UT WoS článku

000322940700003

EID výsledku v databázi Scopus

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