Grubbs Metathesis Enabled by a Light‐Driven <i>gem</i>‐Hydrogenation of Internal Alkynes
Tobias Biberger, Raphael J. Zachmann, Alois Fürstner
Abstract
] (NHC=N-heterocyclic carbene) complexes instigate a light-driven gem-hydrogenation of internal alkynes with concomitant formation of discrete Grubbs-type ruthenium carbene species. This unorthodox reactivity mode is harnessed in the form of a "hydrogenative metathesis" reaction, which converts an enyne substrate into a cyclic alkene. The intervention of ruthenium carbenes formed in the actual gem-hydrogenation step was proven by the isolation and crystallographic characterization of a rather unusual representative of this series carrying an unconfined alkyl group on a disubstituted carbene center.
Topics & Concepts
CarbeneRutheniumAlkeneMetathesisReactivity (psychology)AlkyneChemistryAlkylGrubbs' catalystEnyne metathesisEnyneMedicinal chemistryPhotochemistryCatalysisOrganic chemistryPolymerizationAlternative medicinePolymerMedicinePathologySynthetic Organic Chemistry MethodsChemical Synthesis and AnalysisCatalytic Cross-Coupling Reactions