English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/104462
Share/Impact:
Statistics
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:

Title

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

AuthorsRoca-López, David ; Marqués-López, Eugenia ; Alcaine, Ana ; Merino, Pedro ; Herrera, Raquel P.
Issue Date2014
PublisherRoyal Society of Chemistry
CitationOrganic and Biomolecular Chemistry 12(25): 4503-4510 (2014)
AbstractComputational 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.
Publisher version (URL)http://dx.doi.org/10.1039/C4OB00348A
URIhttp://hdl.handle.net/10261/104462
DOI10.1039/C4OB00348A
ISSN1477-0520
E-ISSN1477-0539
Appears in Collections:(ISQCH) Artículos
Files in This Item:
File Description SizeFormat 
Preprint_A FriedelCrafts.pdf419,66 kBAdobe PDFThumbnail
View/Open
Show full item record
Review this work
 

Related articles:


WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.