Catalytic Olefin Transpositions Facilitated by Ruthenium N,N,N-Pincer Complexes
Alex M. Davies, Kara Greene, Anthony R. Allen, Benjamin M. Farris, Nathaniel K. Szymczak, Corey R. J. Stephenson
Abstract
In this report, we demonstrate olefin transposition/isomerization reactions catalyzed by a series of N,N,N -pincer (1,3-bis(2-pyridylimino)isoindoline) Ru-hydride complexes. The protocol proceeds at room temperature for most substrates, achieving excellent yields, regioselectivity, and diastereoselectivity in short reaction times. The air-stable Ru-chloride derivatives of these complexes exhibit comparable reactivity enabling benchtop setup and synthetic versatility. Furthermore, we demonstrate the potential for one-pot cascade sequences of the products derived from the transposition reactions.
Topics & Concepts
ChemistryRutheniumOlefin fiberPincer movementCatalysisRegioselectivityIsomerizationHydrideReactivity (psychology)Cascade reactionIsoindolineMedicinal chemistryAlkylationCombinatorial chemistryOrganic chemistryHydrogenAlternative medicineMedicinePathologySynthetic Organic Chemistry MethodsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis