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Molecules 2014, 19(2), 1763-1774; doi:10.3390/molecules19021763

Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity

1
Institute for Research in Biomedicine (IRB Barcelona), Baldiri i Reixac, 10. 08028 Barcelona, Spain
2
Department de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain
3
Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, E-46012 Valencia, Spain
4
Department de Química Orgànica, Universitat de Barcelona, Martí i Franqués, 1. 08028 Barcelona, Spain
*
Author to whom correspondence should be addressed.
Received: 2 January 2014 / Revised: 15 January 2014 / Accepted: 27 January 2014 / Published: 3 February 2014
(This article belongs to the Special Issue Fluorine Chemistry 2016)
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Abstract

The scope of the Pauson-Khand reaction (PKR) of internal trifluoromethyl alkynes, previously described with norbornadiene, is expanded to norbornene and ethylene. A thorough structural analysis of the resulting PK adducts has been carried out to unveil that α-trifluoromethylcyclopentenones are preferred in all cases, independently of the electronic properties of the alkyne. The regioselectivity observed with norbornadiene and ethylene is higher than in the case of norbornene.
Keywords: Pauson-Khand reaction; cycloadditions; regioselectivity; cyclopentenones; trifluoromethylalkynes Pauson-Khand reaction; cycloadditions; regioselectivity; cyclopentenones; trifluoromethylalkynes
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Aiguabella, N.; Arce, E.M.; del Pozo, C.; Verdaguer, X.; Riera, A. Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity. Molecules 2014, 19, 1763-1774.

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