Abstract
The catalytic performance of NHC-ligated Ru-indenylidene or benzylidene complexes bearing a tricyclohexylphosphine or a pyridine ligand in ring closing metathesis (RCM), cross metathesis, and ring closing enyne metathesis (RCEYM) reactions is compared. While the PCy3 complexes perform significantly better in RCM and RCEYM reactions than the pyridine complex, all catalysts show similar activity in cross metathesis reactions.
Highlights
Over the past two decades, the olefin metathesis reaction became one of the most important C–C-bond forming reactions in organic synthesis [1]
While ethyl acetate gave a conversion of 75%, which is better than most of the classical solvents, nearly quantitative conversion to the ring closing metathesis (RCM) product was observed in acetic acid
The pyridine ligand is protonated under these conditions which would result in a higher amount of the catalytically active 14-electron species
Summary
Over the past two decades, the olefin metathesis reaction became one of the most important C–C-bond forming reactions in organic synthesis [1]. This result seems to contradict the observations by Adjiman, Taylor et al who reported preparatively useful conversions and yields for second generation Grubbs’ catalyst D in acetic acid [49], their studies were conducted at ambient temperature and for different substrates, while our experiments were conducted at 40 °C.
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