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Sulfoxide‐Chelated Ruthenium Benzylidene Catalyst: a Synthetic Study on the Utility of Olefin Metathesis
Author(s) -
Żukowska Karolina,
Pączek Łukasz,
Grela Karol
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201600538
Subject(s) - ruthenium , catalysis , chemistry , metathesis , sulfoxide , ring closing metathesis , olefin metathesis , salt metathesis reaction , olefin fiber , organic chemistry , solvent , acyclic diene metathesis , combinatorial chemistry , polymerization , polymer
We provide an experimental summary of selected advances in olefin metathesis methodology that were reported over the past decades. A stable and universal sulfoxide‐chelated ruthenium olefin metathesis catalyst [RuCl 2 (SIMes)(=CH−C 6 H 4 −S(O)Ph)], SIMes=1,3‐bis(2,4,6‐trimethylphenyl)‐4,5‐dihydroimidazol‐2‐ylidene, was introduced and its application profile was studied in detail. A range of model substrates of natural origin was developed and successfully metathesized with variants of the reaction, such as ene–yne, cross, or ring‐closing metathesis. All reported reactions were performed in non‐pretreated solvents and in air to demonstrate the user‐friendliness of the system. Besides the great functional group tolerance exhibited by the reported complex, its compatibility with multiple solvents was determined along with its air and moisture stability. Additionally, an interesting effect increasing the reaction efficiency was observed, if reactions were performed at temperatures around the solvent boiling point.