Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines

Herein, we describe an efficient nanocopper-catalyzed Alder-ene reaction of allenynamides. The copper nanoparticles were immobilized on amino-functionalized micro-crystalline 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.

Automated summary

In this study, an efficient nanocopper-catalyzed Alder-ene reaction of allenynamides is described. Copper nanoparticles were immobilized on amino-functionalized micro-crystalline cellulose. The reaction exhibited solvent-controlled chemoselectivity, leading to the synthesis of pyrrolines and pyrroles. The heterogeneous copper catalyst showed high efficiency and recyclability in the Alder-ene reaction, making it a highly attractive catalytic system from an economic and environmental perspective.