2025-04-232025-04-232024-10-16Benítez Narváez, M., Matador Martínez, E., Velázquez Muñoz, M., Lassaletta, J.M., Fernández Fernández, R.F. y Monge Fernández, D. (2024). Organocatalytic Applications of Sulfonyl Squaramides in Anion-Recognition Strategies. European Journal of Organic Chemistry, 27 (47), e202400837. https://doi.org/10.1002/ejoc.202400837.1434-193X1099-0690https://hdl.handle.net/11441/171989A modular, 3-steps protocol for the synthesis of N-sulfonyl squaramides has been developed. The strategic installation of a tetrahedral, electron-withdrawing sulfonyl group into the squaramido core allowed the prevention of undesired self-aggregations, therefore upgrading the solubility in common organic solvents, and moreover, enhancing their H-bond donor abilities for molecular recognition. These unique features have been efficiently exploited in two different ion-pairing reactions: (i) the challenging C4-selective dearomatization of 2-picoline with silyl ketene acetals and (ii) the tritylation of N-methylindole. Furthermore, their catalytic activities have been directly compared with other common and well-established (thio)urea analogues and related H-bond donors, revealing that highly acidic designs are essential to reach optimal catalytic performances.application/pdf5 p.engAttribution-NonCommercial 4.0 Internationalhttp://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccess10.1002/ejoc.202400837