Ruthenium-Catalysed Olefin Metathesis in Environmentally Friendly Solvents: 2-Methyltetrahydrofuran Revisited
PBN-AR
Instytucja
Wydział Chemii (Uniwersytet Warszawski)
Informacje podstawowe
Główny język publikacji
en
Czasopismo
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN
1434-193X
EISSN
1099-0690
Wydawca
WILEY-BLACKWELL
DOI
URL
Rok publikacji
2019
Numer zeszytu
4
Strony od-do
640-646
Numer tomu
2019
Link do pełnego tekstu
Identyfikator DOI
Liczba arkuszy
Streszczenia
Język
en
Treść
Application profiles of a set of popular second-generation ruthenium catalysts were experimentally investigated in an environmentally friendly solvent, 2-methyltetrahydrofuran (2-MeTHF), and compared with the activity of the same catalysts in toluene, a popular solvent used in industrial olefin metathesis. It was found that a catalyst containing a 2-isopropoxy-5- nitrobenzylidene moiety and a symmetrical N-heterocyclic (NHC) ligand with 2,6-diisopropylphenyl substituents (SIPr) ex- Introduction Catalytic olefin metathesis[1] utilising modern, well-defined catalysts is a powerful transformation in organic chemistry allowing to form carbon–carbon double bonds selectively and in practically unlimited structural arrangements, thus offering great promises for fine chemical and pharmaceutical synthesis.[ 2] Historically, olefin metathesis reactions were carried out in toxic solvents, such as dichloromethane (DCM), 1,2-dichloroethane (DCE), chloroform, benzene and other aromatic solvents.[ 1] As pointed out recently by Sherwood, the use of chlorinated solvents soon will be banned (or are prohibited already) and the society of chemists must adapt to.[3] This is especially the case in the pharmaceutical production, which is not truly material-efficient (high E-factor values)[4] and uses large amounts of solvents.[5] Therefore, finding more environmentally friendly equivalents of these solvents in order to fulfil the principles of green chemistry is of highest importance.[6–9] A number of reports proving the compatibility of modern ruthenium olefin metathesis catalysts with alternative reaction media, such as water,[10] ethanol,[11] ionic liquids,[12] supercritical carbon dioxide (scCO2),[13–15] glycerol,[16] polyethylene glycol,[ 17] dimethyl carbonate (DMC),[18–20] methyl decanoate,[21] ethyl acetate (EtOAc),[22] cyclopentyl methyl ether (CPME)[22] and other solvents appeared in the recent literature.[23] Surpris- [a] Biological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw Żwirki i Wigury 101, 02-089 Warsaw, Poland E-mail: karol.grela@gmail.com anna.kajetanowicz@gmail.com www.karolgrela.eu [b] Centre of New Technologies, University of Warsaw S. Banacha 2c, 02-097 Warszawa, Poland Supporting information and ORCID(s) from the author(s) for this article are available on the WWW under https://doi.org/10.1002/ejoc.201801741. Eur. J. Org. Chem. 2019, 640–646 640 © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim hibits the highest catalytic activity in 2-MeTHF also at a lower temperature (30 °C). Ab initio studies showed that initiation rates of Ru catalysts bearing NHC ligands in 2-MeTHF can be correlated with partial charges and bond lengths between selected crucial atoms in the studied ruthenium complexes. The results demonstrate that aromatic or chlorinated solvents, typically used in metathesis reactions, can be successfully replaced in many cases by 2-MeTHF.
Cechy publikacji
Original article
Original article presents the results of original research or experiment
Oryginalny artykuł naukowy
Oryginalny artykuł naukowy przedstawia rezultaty oryginalnych badań naukowych lub eksperymentu.
Inne
System-identifier
PX-5c84da6cd5de4ffe79b8e7c1
CrossrefMetadata from Crossref logo
Cytowania
Liczba prac cytujących tę pracę
Brak danych
Referencje
Liczba prac cytowanych przez tę pracę
Brak danych