Publication: A Thiourea-based Rotaxane Catalyst: Nucleophilic Fluorination Phase-Transfer Process Unlocked by the Mechanical Bond
Authors
Martínez Cuezva, Alberto ; Berná Cánovas, José ; Puigcerver Alarcón, Julio ; Juan S. Santiago Dato ; Alajarín Cerón, Mateo
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Publisher
American Chemical Society
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DOI
https://doi.org/10.1021/acs.orglett.5c00411
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info:eu-repo/semantics/article
Description
Abstract
We 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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