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A Click Strategy for the Immobilization of MacMillan Organocatalysts onto Polymers and Magnetic Nanoparticles
- Riente, Paola, Yadav, Jagjit, Pericàs, Miquel A.
- Organic letters 2012 v.14 no.14 pp. 3668-3671
- aldehydes, alkylation, alkynes, azides, catalysts, catalytic activity, chemical structure, enantioselectivity, iron oxides, magnetism, nanoparticles, polymers, pyrroles
- A chemically modified, first generation MacMillan imidazolidin-4-one has been anchored onto 1% DVB Merrifield resin and Fe₃O₄ (5.3 ± 1.4 nm) magnetic nanoparticles through copper-catalyzed alkyne azide cycloaddition (CuAAC) reactions. The resulting immobilized catalysts have been successfully used in the asymmetric Friedel–Crafts alkylation of N-substituted pyrroles with α,β-unsaturated aldehydes. The PS-supported catalyst (B) showed higher catalytic activity and enantioselectivity, while the MNP-supported one (A) showed higher recyclability and could be used in a sequential process with intermediate magnetic decantation.