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Issue 25, 2014
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A Friedel–Crafts alkylation mechanism using an aminoindanol-derived thiourea catalyst

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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

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Publication details

The article was received on 14 Feb 2014, accepted on 09 Apr 2014 and first published on 09 Apr 2014


Article type: Paper
DOI: 10.1039/C4OB00348A
Citation: Org. Biomol. Chem., 2014,12, 4503-4510
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    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

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