Redox-Neutral Ru(0)-Catalyzed Alkenylation of 2-Carboxaldimine-heterocyclopentadienes
Roberto Sala, Gredy Kiala, Luı́s F. Veiros, Gianluigi Broggini, Giovanni Poli, Julie Oble
Abstract
A new Ru3(CO)12-catalyzed directed alkenylation of 2-carboxaldimine-heterocyclopentadienes has been accomplished. This process allows coupling of furan, pyrrole, indole, and thiophene 2-carboxaldimines with electron-poor alkenes such as acrylates, vinylsulfones, and styrenes. This regio- and chemoselective oxidative C–H coupling does not require the presence of an additional sacrificial oxidant. Density functional theory calculations allowed us to propose a mechanism and unveiled the nature of the H2 acceptor.
Topics & Concepts
FuranThiophenePyrroleCatalysisChemistryOxidative phosphorylationIndole testDensity functional theoryOxidative coupling of methaneRedoxPhotochemistryElectron acceptorAcceptorCombinatorial chemistryMedicinal chemistryComputational chemistryStereochemistryOrganic chemistryBiochemistryCondensed matter physicsPhysicsCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCyclopropane Reaction Mechanisms