Backbone tuning in indenylidene–ruthenium complexes bearing an unsaturated N-heterocyclic carbene

• Main Authors: César A. Urbina-Blanco, Xavier Bantreil, Hervé Clavier, Alexandra M. Z. Slawin, Steven P. Nolan
• Format: Article
• Language: English
• Published: Beilstein-Institut 2010-11-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: N-heterocyclic carbene; olefin metathesis; percent buried volume; ruthenium–indenylidene; Tolman electronic parameter
• Online Access: https://doi.org/10.3762/bjoc.6.128
• ISSN: 1860-5397

The steric and electronic influence of backbone substitution in IMes-based (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene) N-heterocyclic carbenes (NHC) was probed by synthesizing the [RhCl(CO)2(NHC)] series of complexes to quantify experimentally the Tolman electronic parameter (electronic) and the percent buried volume (%Vbur, steric) parameters. The corresponding ruthenium–indenylidene complexes were also synthesized and tested in benchmark metathesis transformations to establish possible correlations between reactivity and NHC electronic and steric parameters.