Gold-catalyzed synthesis of β-trifluoromethylated α,β-unsaturated ketones from CF3-substituted propargylic carboxylates and their reactivity in Diels-Alder reactions

Arnaud Boreux 1, 2, * Aubin Lambion 2 Dominic Campeau 3 Marina Sanita 3 Ruben Coronel 3 Olivier Riant 2, * Fabien Gagosz 1, 3, *
* Corresponding author
1 DCSO - Laboratoire de synthèse organique
2 IMCN - Institut de la matière condensée et des nanosciences / Institute of Condensed Matter and Nanosciences
3 Department of Chemistry and Biomolecular Sciences University of Ottawa, D'lorio Hall
Abstract : The synthesis of fluorinated synthetic intermediates has become a field of intense research in organic chemistry. In this article, we report the application of a gold-catalyzed rearrangement to the synthesis of β-trifluoromethylated α,β-unsaturated ketones. The scope of the reaction, as well as the valorization of the products in subsequent transformations has been investigated. This study allowed for the preparation of various CF3-substituted enones and fluorinated Diels-Alder adducts from easily accessible starting materials.
Keywords : Gold catalysis α β-unsaturated ketones Trifluoromethyl group Propargylic acetates
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Journal articles
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https://hal-polytechnique.archives-ouvertes.fr/hal-02096386
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Submitted on : Thursday, April 11, 2019 - 12:08:48 PM
Last modification on : Saturday, April 13, 2019 - 1:18:12 AM

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Arnaud Boreux, Aubin Lambion, Dominic Campeau, Marina Sanita, Ruben Coronel, et al.. Gold-catalyzed synthesis of β-trifluoromethylated α,β-unsaturated ketones from CF3-substituted propargylic carboxylates and their reactivity in Diels-Alder reactions. Tetrahedron, Elsevier, 2018, 74 (38), pp.5232-5239. ⟨10.1016/j.tet.2018.05.054⟩. ⟨hal-02096386⟩

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