Person: Puigcerver Alarcón, Julio
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Puigcerver Alarcón, Julio
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Universidad de Murcia. Departamento de Química Orgánica
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- PublicationOpen AccessOptimizing an Organocatalyzed Process in an Undergraduate Laboratory: A Solvent Screening(American Chemical Society, 2019-11-19) Puigcerver Alarcón, Julio; Martínez Cuezva, Alberto; Química OrgánicaIn this undergraduate organic laboratory study, an extensive solvent screening has been 10 meticulously designed for the optimization of the L-proline-organocatalyzed intermolecular aldol reaction involving acetone and p-nitrobenzaldehyde. The experimental procedure entailed selecting specific solvents, analyzing the reaction crude through NMR spectroscopy, and subsequently, purifying the aldol adducts to measure their enantiomeric ratios via HPLC provided with chiral column. Remarkably, this comprehensive investigation was efficiently conducted within two concise 2-hour 15 laboratory sessions, together with 1-hour seminar session, rendering it highly suitable for both Bachelor's and Master's degree programs. Conducted at room temperature, the experiments unveiled significant variations in both yields and enantiomeric excess of the aldol products, and the byproducts proportions, depending on the solvent of choice. This experiential learning opportunity empowers students to gain practical insights into organocatalyzed transformations, purification techniques, and 20 chromatographic analysis, enhancing their proficiency as organic chemists.
- PublicationOpen AccessA Thiourea-based Rotaxane Catalyst: Nucleophilic Fluorination Phase-Transfer Process Unlocked by the Mechanical Bond(American Chemical Society, 2025-03-18) Martínez Cuezva, Alberto; Berná Cánovas, José; Puigcerver Alarcón, Julio; Juan S. Santiago Dato; Alajarín Cerón, Mateo; Química OrgánicaWe report a five-component clipping approach using activated isophthaloyl-derived esters to synthesize an amide-based thiourea rotaxane. This method overcomes acyl chloride limitations with nucleophilic thiourea threads. The steric hindrance of the mechanical bond enables, for the first time, an interlocked thiourea as a hydrogen-bonding phase-transfer organocatalyst in nu-cleophilic fluorinations. This highlights how mechanical bonds expand thiourea catalysis to processes previously incompatible with conventional catalysts.
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