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.
Highlights
We describe an efficient nanocoppercatalyzed Alder-ene reaction of allenynamides
In our initial attempts to examine the reactivity of allenynamides, an analogous Pd(II)-catalyzed cycloisomerization without the aid of oxidant was observed, leading to the formation of pyrrolines (2,5-dihydropyrroles) and pyrroles
Given the surging interest in green and sustainable nanocatalysts, we were motivated to investigate the catalytic activity of copper nanoparticles immobilized on microcrystalline cellulose (MCC) in the Alder-ene reaction of allenynamides (Scheme 1c)
Summary
We describe an efficient nanocoppercatalyzed Alder-ene reaction of allenynamides. Given the surging interest in green and sustainable nanocatalysts, we were motivated to investigate the catalytic activity of copper nanoparticles immobilized on microcrystalline cellulose (MCC) in the Alder-ene reaction of allenynamides (Scheme 1c).
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