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Comparative Investigation of Hoveyda–Grubbs Catalysts bearing Modified N ‐ Heterocyclic Carbene Ligands
Author(s) -
Ledoux Nele,
Linden Anthony,
Allaert Bart,
Mierde Hans Vander,
Verpoort Francis
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700042
Subject(s) - carbene , chemistry , romp , metathesis , alkyl , ring opening metathesis polymerisation , catalysis , steric effects , acyclic diene metathesis , ligand (biochemistry) , medicinal chemistry , polymerization , organic chemistry , combinatorial chemistry , polymer , biochemistry , receptor
This paper reports the structural modification of Hoveyda–Grubbs complexes through the introduction of either an N ‐alkyl‐ N′ ‐mesityl heterocyclic carbene, an N ‐alkyl‐ N′ ‐(2,6‐diisopropylphenyl) heterocyclic carbene, or an N ‐alkyl‐ N′ ‐alkyl heterocyclic carbene. The effect of the modified N‐heterocyclic carbene (NHC) ligand was investigated in representative ring‐opening metathesis polymerization (ROMP), ring‐closing metathesis (RCM) and cross metathesis (CM) reactions. A pronounced influence on both catalyst activity and selectivity was found to be exerted by the NHC amino substituents, which emphasizes that a rigorously selected steric environment is critical in olefin metathesis catalyst design.