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Towards Long‐Living Metathesis Catalysts by Tuning the N‐Heterocyclic Carbene (NHC) Ligand on Trifluoroacetamide‐Activated Boomerang Ru Complexes
Author(s) -
Clavier Hervé,
Caijo Fréderic,
Borré Etienne,
Rix Diane,
Boeda Fabien,
Nolan Steven P.,
Mauduit Marc
Publication year - 2009
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.200900407
Subject(s) - carbene , chemistry , enyne metathesis , metathesis , catalysis , ligand (biochemistry) , steric effects , ring closing metathesis , combinatorial chemistry , salt metathesis reaction , ruthenium , ring opening metathesis polymerisation , organic chemistry , medicinal chemistry , polymerization , biochemistry , polymer , receptor
The synthesis and characterization of three novel trifluoromethylamido‐containing “boomerang” precatalysts bearing various N‐heterocyclic carbene (NHC) ligands are reported. Comparative kinetic and stability studies show the significant effect of the NHC on the catalyst reaction profile. An investigation of the reaction scope for diverse metathesis transformations has allowed us to establish the influence of the NHC on catalyst activity, especially as a function of substrate steric bulk. The excellent stability of one of the novel precatalysts is disclosed, and allowed for its recovery at the end of catalytic reactions. Large‐scale ring‐closing metathesis, enyne‐metathesis and cross‐metathesis experiments have revealed the recoverability of the catalyst. ICP‐MS analyses of the synthesized products reveal Ru contamination levels of less than 2.5 ppm.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)