Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/104462
COMPARTIR / EXPORTAR:
logo share SHARE logo core CORE BASE
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE

Invitar a revisión por pares abierta
Título

A Friedel–Crafts alkylation mechanism using an aminoindanol-derived thiourea catalyst

AutorRoca-López, David CSIC ORCID; Marqués-López, Eugenia CSIC ORCID; Alcaine, Ana CSIC; Merino, Pedro CSIC ORCID ; Herrera, Raquel P. CSIC ORCID
Fecha de publicación2014
EditorRoyal Society of Chemistry (UK)
CitaciónOrganic and Biomolecular Chemistry 12(25): 4503-4510 (2014)
ResumenComputational calculations based on experimental results shed light on the mechanistic proposal for a Friedel–Crafts alkylation reaction between indole and nitroalkenes, catalysed by a chiral aminoindanol-derived thiourea. In our hypothesis both substrates are simultaneously coordinated to the catalyst in a bifunctional mode. This study elucidates the crucial role played by the hydroxyl group of the catalyst in the success of the reaction. The OH group seems to be involved in the preferential attack of the indole over the nitroalkene, affording the major enantiomer and stabilizing the resulting transition state by a concomitant coordination with the nitroolefin. The results obtained with other catalysts from the same family, and other indoles, are reported and discussed. Theoretical calculations are in agreement with the experimental outcomes and with our previously developed mechanism, displaying the pivotal role played by hydrogen bond interactions.
Versión del editorhttp://dx.doi.org/10.1039/C4OB00348A
URIhttp://hdl.handle.net/10261/104462
DOI10.1039/C4OB00348A
ISSN1477-0520
E-ISSN1477-0539
Aparece en las colecciones: (ISQCH) Artículos




Ficheros en este ítem:
Fichero Descripción Tamaño Formato
Preprint_A FriedelCrafts.pdf419,66 kBAdobe PDFVista previa
Visualizar/Abrir
Mostrar el registro completo

CORE Recommender

WEB OF SCIENCETM
Citations

27
checked on 27-feb-2024

Page view(s)

369
checked on 19-mar-2024

Download(s)

431
checked on 19-mar-2024

Google ScholarTM

Check

Altmetric

Altmetric


NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.