Jump to main content
Jump to site search

Issue 25, 2014
Previous Article Next Article

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

Author affiliations

Abstract

Computational 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.

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

Back to tab navigation

Supplementary files

Article information


Submitted
14 Feb 2014
Accepted
09 Apr 2014
First published
09 Apr 2014

Org. Biomol. Chem., 2014,12, 4503-4510
Article type
Paper
Author version available

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

D. Roca-López, E. Marqués-López, A. Alcaine, P. Merino and R. P. Herrera, Org. Biomol. Chem., 2014, 12, 4503
DOI: 10.1039/C4OB00348A

Social activity

Search articles by author

Spotlight

Advertisements