The Impact of Water on Ru-Catalyzed Olefin Metathesis: Potent Deactivating Effects Even at Low Water Concentrations
Christian O. Blanco, Joshua M. Sims, Daniel L. Nascimento, Alexandre Y. Goudreault, Stephan N. Steinmann, Carine Michel, Deryn E. Fogg
Abstract
) were most affected. Maximum water tolerance was exhibited by slowly initiating iodide and cyclic (alkyl)(amino)carbene (CAAC) derivatives. Computational investigations indicated that hydrogen bonding of water to substrate can also play a role, by retarding cyclization relative to decomposition. These results have important implications for olefin metathesis in organic media, where water is a ubiquitous contaminant, and for aqueous metathesis, which currently requires superstoichiometric "catalyst" for demanding reactions.
Topics & Concepts
CatalysisCarbeneChemistryRutheniumMetathesisOlefin metathesisDecompositionOlefin fiberCombinatorial chemistrySalt metathesis reactionSubstrate (aquarium)Organic chemistryPolymerizationOceanographyGeologyPolymerSynthetic Organic Chemistry MethodsFuel Cells and Related MaterialsOrganometallic Complex Synthesis and Catalysis