Hydrazone and Oxime Olefination via Ruthenium Alkylidenes
Daniel J. Nasrallah, Troy E. Zehnder, Jacob R. Ludwig, Daniel C. Steigerwald, John J. Kiernicki, Nathaniel K. Szymczak, Corinna S. Schindler
Abstract
Abstract We describe the development of an efficient method for the olefination of hydrazones and oximes. The key design approach that enables this transformation is tuning of the energy/polarity of C=N π‐bonds by employing heteroatom functionalities (NR 2 , OR). The resulting hydrazones or oximes facilitate olefination with ruthenium alkylidenes. Through this approach, we show that air‐stable, commercially available ruthenium alkylidenes provide access to functionalized alkenes (20 examples) in ring‐closing reactions with yields up to 88 %.
Topics & Concepts
RutheniumOximeHydrazoneHeteroatomCombinatorial chemistryChemistryClosing (real estate)Ring (chemistry)Organic chemistryCatalysisPolitical scienceLawSynthetic Organic Chemistry MethodsAdvanced Synthetic Organic ChemistrySynthesis and Catalytic Reactions