RT info:eu-repo/semantics/article
T1 Tailored Catalysts Based on Polymers of Intrinsic Microporosity for Asymmetric Aza-Henry Reaction of Pyrazolinone Ketimines in Batch and Flow
A1 Sánchez Molpeceres, Rodrigo
A1 Zhan, Paolo
A1 Martín Maroto, Laura
A1 Maestro Fernández, Alicia
A1 Miguel García, Jesús Ángel
A1 Comesaña Gandara, Bibiana
A1 Andrés García, José María
K1 Polímeros de microporosidad intrínseca
K1 Catalizador heterogéneo
K1 Tiourea derivada de la quinina
K1 Aza-Henry asimétrico
K1 Cetiminas de pirazolinona
K1 Flujo continuo
AB We report the design and application of heterogeneous organocatalysts based on polymers of intrinsic microporosity (PIMs) for the asymmetric aza-Henry reaction of N-Boc-protected pyrazolinone ketimines with nitromethane. Two copolymers (PIM-10 and PIM-20) incorporating a flexible isatin-derived monomer were synthesized and postfunctionalized with a quinine-derived thiourea. The resulting materials, PIM-10-TU and PIM-20-TU, exhibited high thermal stability, tailored porosity, and effective enantioselective catalytic performance in batch- and continuous-flow conditions. PIM-10-TU showed superior activity and recyclability, achieving full conversion in 2–4 h and affording β-nitroamine derivatives in up to 87% yield and 85:15 er. Flow experiments enabled gram-scale synthesis with short residence times and a sustained efficiency. The synthetic utility of the chiral aminopyrazolones was demonstrated via derivatization to ureas and thioureas without erosion of the enantiopurity. This study highlights the potential of PIM-supported organocatalysts as robust and recyclable platforms for asymmetric synthesis under sustainable conditions.
PB American Chemical Society
SN 2637-6105
YR 2025
FD 2025
LK https://uvadoc.uva.es/handle/10324/79404
UL https://uvadoc.uva.es/handle/10324/79404
LA eng
NO ACS Applied Polymer Materials, 2025, vol. 7, n. 20, p. 13626-13636.
NO Producción Científica
DS UVaDOC
RD 28-nov-2025