Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines
Zhiyao Zheng, Luca Deiana, Daniels Posevins, Abdolrahim A. Rafi, Kaiheng Zhang, Magnus J. Johansson, Cheuk‐Wai Tai, Armando Córdova, Jan‐E. Bäckvall
Abstract
Herein, we describe an efficient nanocopper-catalyzed Alder-ene reaction of allenynamides. The copper nanoparticles were immobilized on amino-functionalized microcrystalline cellulose. A solvent-controlled chemoselectivity of the reaction was observed, leading to the chemodivergent synthesis of pyrrolines (2,5-dihydropyrroles) and pyrroles. The heterogeneous copper catalyst exhibits high efficiency and good recyclability in the Alder-ene reaction, constituting a highly attractive catalytic system from an economical and environmental point of view.
Topics & Concepts
CatalysisChemoselectivityEne reactionCopperChemistryMicrocrystalline celluloseDiels–Alder reactionHeterogeneous catalysisOrganic chemistryCombinatorial chemistryCelluloseCatalytic Cross-Coupling ReactionsCatalysis for Biomass ConversionSynthesis and Characterization of Pyrroles