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Ruthenium‐Catalysed Olefin Metathesis in Environmentally Friendly Solvents: 2‐Methyltetrahydrofuran Revisited
Author(s) -
Smoleń Michał,
Marczyk Anna,
Kośnik Wioletta,
Trzaskowski Bartosz,
Kajetanowicz Anna,
Grela Karol
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801741
Subject(s) - ruthenium , chemistry , catalysis , moiety , metathesis , salt metathesis reaction , ligand (biochemistry) , olefin metathesis , toluene , solvent , olefin fiber , organic chemistry , photochemistry , polymerization , polymer , biochemistry , receptor
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) exhibits 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.