A Macrocyclic Ruthenium Carbene for Size-Selective Alkene Metathesis
Yutong Zhang, Steven T. Diver
Abstract
The synthesis of a macrocyclic Ru carbene catalyst for selective cross alkene metathesis is reported. The new catalyst showed different reactivity for various type 1 alkenes in homodimerization which correlated with the aggregrate size of the allylic substituent. The altered reactivity profile allowed for selective product formation in competition cross alkene metathesis between two different type 1 alkenes and tert-butyl acrylate. Selectivity in these reactions is attributed to the ability of the macrocyclic catalyst to differentiate alkenes based on their size. Two preparative examples of cross metathesis with the macrocyclic catalyst are also provided.
Topics & Concepts
ChemistryAlkeneCarbeneMetathesisReactivity (psychology)RutheniumGrubbs' catalystCatalysisAcyclic diene metathesisAllylic rearrangementSalt metathesis reactionSubstituentSelectivityOrganic chemistryMedicinal chemistryPolymerizationPolymerAlternative medicinePathologyMedicineSynthetic Organic Chemistry MethodsN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCyclopropane Reaction Mechanisms