Urea activation by an external brønsted acid: Breaking self-association and tuning catalytic performance

Giménez Sonsona, I. ; Marqués-López, E. (Universidad de Zaragoza) ; Häring, M. ; Díaz, D. ; Pérez Herrera, R. (Universidad de Zaragoza)

Resumen: In this work, we hypothesize that Brønsted acids can activate urea-based catalysts by diminishing its self-assembly tendency. As a proof of concept, we used the asymmetric Friedel–Crafts alkylation of indoles with nitroalkenes as a benchmark reaction. The resulting 3-substituted indole derivatives were obtained with better results due to cooperative effects of the chiral urea and a Brønsted acid additive. Such synergy has been rationalized in terms of disassembly of the supramolecular catalyst aggregates, affording a more acidic and rigid catalytic complex.

Idioma: Inglés

DOI: 10.3390/catal8080305

Año: 2018

Publicado en: CATALYSTS 8, 8 (2018), 305 [21 pp]
ISSN: 2073-4344

Factor impacto JCR: 3.444 (2018)

Categ. JCR: CHEMISTRY, PHYSICAL rank: 57 / 148 = 0.385 (2018) - Q2 - T2

Factor impacto SCIMAGO: 0.853 - Physical and Theoretical Chemistry (Q2) - Catalysis (Q2)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E07-17R
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-88091-P
Financiación: info:eu-repo/grantAgreement/ES/UZ/JIUZ-2017-CIE-05

Tipo y forma: Article (Published version)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)