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

Arnaud Boreux; Aubin Lambion; Dominic Campeau; Marina Sanita; Ruben Coronel; Olivier Riant; Fabien Gagosz

doi:10.1016/j.tet.2018.05.054

Journal articles

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

Domain :

Chemical Sciences / Organic chemistry

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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

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

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

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